From 3745cd2b4c71f3a0f6908b8ea6216b6e24728868 Mon Sep 17 00:00:00 2001
From: Amogh Sunil <stealthwhiz@gmail.com>
Date: Wed, 1 Jul 2026 12:58:25 +0530
Subject: [PATCH 1/4] feat: add compression layer for token optimization
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

- SmartCrusher: compress JSON tool outputs (removes nulls, deduplicates arrays, truncates strings)
- CodeCompressor: strip comments and blank lines from source files (TS, JS, Py, Go, Rust, Java, C++)
- CacheAligner: order system prompt static-first to maximize provider KV cache hits
- doc-converter: convert PDF, DOCX, XLSX, PPTX to clean markdown via pdf-parse, mammoth, xlsx, jszip
- doc-store + CCR: chunk large docs into sections, return outline first, agent fetches on demand
- Disk cache for converted docs at memory/.doc-cache/ with source-newer-than-cache invalidation
- Fix: check isConvertible() by extension before isBinary() — PDFs without null bytes were bypassing conversion
- Add benchmark scripts: test-compression.mjs, test-live-benchmark.mjs, test-token-proof.mjs
---
 package-lock.json                  | 590 +++++++++++++++++++++++++++++
 package.json                       |   7 +
 src/compression/cache-aligner.ts   |  87 +++++
 src/compression/code-compressor.ts | 166 ++++++++
 src/compression/index.ts           |   8 +
 src/compression/smart-crusher.ts   | 140 +++++++
 src/cost-tracker.ts                |  13 +
 src/loader.ts                      |  75 ++--
 src/sdk.ts                         |   4 +
 src/tools/cli.ts                   |   9 +
 src/tools/doc-converter.ts         | 231 +++++++++++
 src/tools/doc-store.ts             | 152 ++++++++
 src/tools/index.ts                 |  43 ++-
 src/tools/read.ts                  | 124 +++++-
 test-compression.mjs               | 184 +++++++++
 test-live-benchmark.mjs            | 210 ++++++++++
 test-token-proof.mjs               | 195 ++++++++++
 17 files changed, 2200 insertions(+), 38 deletions(-)
 create mode 100644 src/compression/cache-aligner.ts
 create mode 100644 src/compression/code-compressor.ts
 create mode 100644 src/compression/index.ts
 create mode 100644 src/compression/smart-crusher.ts
 create mode 100644 src/tools/doc-converter.ts
 create mode 100644 src/tools/doc-store.ts
 create mode 100644 test-compression.mjs
 create mode 100644 test-live-benchmark.mjs
 create mode 100644 test-token-proof.mjs

diff --git a/package-lock.json b/package-lock.json
index 2316271..8af62c1 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -22,8 +22,13 @@
         "@opentelemetry/sdk-trace-node": "^2.7.0",
         "@opentelemetry/semantic-conventions": "^1.40.0",
         "@sinclair/typebox": "^0.34.41",
+        "headroom-ai": "^0.22.4",
         "js-yaml": "^4.1.0",
+        "jszip": "^3.10.1",
+        "mammoth": "^1.12.0",
         "node-cron": "^3.0.3",
+        "pdf-parse": "^2.4.5",
+        "xlsx": "^0.18.5",
         "yaml": "^2.8.2"
       },
       "bin": {
@@ -31,8 +36,10 @@
       },
       "devDependencies": {
         "@types/js-yaml": "^4.0.9",
+        "@types/jszip": "^3.4.0",
         "@types/node": "^22.0.0",
         "@types/node-cron": "^3.0.11",
+        "@types/pdf-parse": "^1.1.5",
         "typescript": "^5.7.0"
       },
       "engines": {
@@ -596,6 +603,190 @@
         "zod-to-json-schema": "^3.25.0"
       }
     },
+    "node_modules/@napi-rs/canvas": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas/-/canvas-0.1.80.tgz",
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+      "license": "MIT",
+      "workspaces": [
+        "e2e/*"
+      ],
+      "engines": {
+        "node": ">= 10"
+      },
+      "optionalDependencies": {
+        "@napi-rs/canvas-android-arm64": "0.1.80",
+        "@napi-rs/canvas-darwin-arm64": "0.1.80",
+        "@napi-rs/canvas-darwin-x64": "0.1.80",
+        "@napi-rs/canvas-linux-arm-gnueabihf": "0.1.80",
+        "@napi-rs/canvas-linux-arm64-gnu": "0.1.80",
+        "@napi-rs/canvas-linux-arm64-musl": "0.1.80",
+        "@napi-rs/canvas-linux-riscv64-gnu": "0.1.80",
+        "@napi-rs/canvas-linux-x64-gnu": "0.1.80",
+        "@napi-rs/canvas-linux-x64-musl": "0.1.80",
+        "@napi-rs/canvas-win32-x64-msvc": "0.1.80"
+      }
+    },
+    "node_modules/@napi-rs/canvas-android-arm64": {
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+        "riscv64"
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+      "optional": true,
+      "os": [
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+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-linux-x64-gnu": {
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+        "x64"
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+      "optional": true,
+      "os": [
+        "linux"
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+      "engines": {
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+      }
+    },
+    "node_modules/@napi-rs/canvas-linux-x64-musl": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-linux-x64-musl/-/canvas-linux-x64-musl-0.1.80.tgz",
+      "integrity": "sha512-x0XvZWdHbkgdgucJsRxprX/4o4sEed7qo9rCQA9ugiS9qE2QvP0RIiEugtZhfLH3cyI+jIRFJHV4Fuz+1BHHMg==",
+      "cpu": [
+        "x64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-win32-x64-msvc": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-win32-x64-msvc/-/canvas-win32-x64-msvc-0.1.80.tgz",
+      "integrity": "sha512-Z8jPsM6df5V8B1HrCHB05+bDiCxjE9QA//3YrkKIdVDEwn5RKaqOxCJDRJkl48cJbylcrJbW4HxZbTte8juuPg==",
+      "cpu": [
+        "x64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "win32"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
     "node_modules/@nodable/entities": {
       "version": "2.1.1",
       "resolved": "https://registry.npmjs.org/@nodable/entities/-/entities-2.1.1.tgz",
@@ -1748,6 +1939,16 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/@types/jszip": {
+      "version": "3.4.0",
+      "resolved": "https://registry.npmjs.org/@types/jszip/-/jszip-3.4.0.tgz",
+      "integrity": "sha512-GFHqtQQP3R4NNuvZH3hNCYD0NbyBZ42bkN7kO3NDrU/SnvIZWMS8Bp38XCsRKBT5BXvgm0y1zqpZWp/ZkRzBzg==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "jszip": "*"
+      }
+    },
     "node_modules/@types/node": {
       "version": "22.19.20",
       "resolved": "https://registry.npmjs.org/@types/node/-/node-22.19.20.tgz",
@@ -1764,12 +1965,31 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/@types/pdf-parse": {
+      "version": "1.1.5",
+      "resolved": "https://registry.npmjs.org/@types/pdf-parse/-/pdf-parse-1.1.5.tgz",
+      "integrity": "sha512-kBfrSXsloMnUJOKi25s3+hRmkycHfLK6A09eRGqF/N8BkQoPUmaCr+q8Cli5FnfohEz/rsv82zAiPz/LXtOGhA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/node": "*"
+      }
+    },
     "node_modules/@types/retry": {
       "version": "0.12.0",
       "resolved": "https://registry.npmjs.org/@types/retry/-/retry-0.12.0.tgz",
       "integrity": "sha512-wWKOClTTiizcZhXnPY4wikVAwmdYHp8q6DmC+EJUzAMsycb7HB32Kh9RN4+0gExjmPmZSAQjgURXIGATPegAvA==",
       "license": "MIT"
     },
+    "node_modules/@xmldom/xmldom": {
+      "version": "0.8.13",
+      "resolved": "https://registry.npmjs.org/@xmldom/xmldom/-/xmldom-0.8.13.tgz",
+      "integrity": "sha512-KRYzxepc14G/CEpEGc3Yn+JKaAeT63smlDr+vjB8jRfgTBBI9wRj/nkQEO+ucV8p8I9bfKLWp37uHgFrbntPvw==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=10.0.0"
+      }
+    },
     "node_modules/acorn": {
       "version": "8.16.0",
       "resolved": "https://registry.npmjs.org/acorn/-/acorn-8.16.0.tgz",
@@ -1791,6 +2011,15 @@
         "acorn": "^8"
       }
     },
+    "node_modules/adler-32": {
+      "version": "1.3.1",
+      "resolved": "https://registry.npmjs.org/adler-32/-/adler-32-1.3.1.tgz",
+      "integrity": "sha512-ynZ4w/nUUv5rrsR8UUGoe1VC9hZj6V5hU9Qw1HlMDJGEJw5S7TfTErWTjMys6M7vr0YWcPqs3qAr4ss0nDfP+A==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
     "node_modules/agent-base": {
       "version": "7.1.4",
       "resolved": "https://registry.npmjs.org/agent-base/-/agent-base-7.1.4.tgz",
@@ -1880,6 +2109,12 @@
         "node": "*"
       }
     },
+    "node_modules/bluebird": {
+      "version": "3.4.7",
+      "resolved": "https://registry.npmjs.org/bluebird/-/bluebird-3.4.7.tgz",
+      "integrity": "sha512-iD3898SR7sWVRHbiQv+sHUtHnMvC1o3nW5rAcqnq3uOn07DSAppZYUkIGslDz6gXC7HfunPe7YVBgoEJASPcHA==",
+      "license": "MIT"
+    },
     "node_modules/bowser": {
       "version": "2.14.1",
       "resolved": "https://registry.npmjs.org/bowser/-/bowser-2.14.1.tgz",
@@ -1892,6 +2127,19 @@
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       "license": "BSD-3-Clause"
     },
+    "node_modules/cfb": {
+      "version": "1.2.2",
+      "resolved": "https://registry.npmjs.org/cfb/-/cfb-1.2.2.tgz",
+      "integrity": "sha512-KfdUZsSOw19/ObEWasvBP/Ac4reZvAGauZhs6S/gqNhXhI7cKwvlH7ulj+dOEYnca4bm4SGo8C1bTAQvnTjgQA==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "adler-32": "~1.3.0",
+        "crc-32": "~1.2.0"
+      },
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
     "node_modules/chalk": {
       "version": "5.6.2",
       "resolved": "https://registry.npmjs.org/chalk/-/chalk-5.6.2.tgz",
@@ -1924,6 +2172,15 @@
         "node": ">=12"
       }
     },
+    "node_modules/codepage": {
+      "version": "1.15.0",
+      "resolved": "https://registry.npmjs.org/codepage/-/codepage-1.15.0.tgz",
+      "integrity": "sha512-3g6NUTPd/YtuuGrhMnOMRjFc+LJw/bnMp3+0r/Wcz3IXUuCosKRJvMphm5+Q+bvTVGcJJuRvVLuYba+WojaFaA==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
     "node_modules/color-convert": {
       "version": "2.0.1",
       "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-2.0.1.tgz",
@@ -1942,6 +2199,24 @@
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       "license": "MIT"
     },
+    "node_modules/core-util-is": {
+      "version": "1.0.3",
+      "resolved": "https://registry.npmjs.org/core-util-is/-/core-util-is-1.0.3.tgz",
+      "integrity": "sha512-ZQBvi1DcpJ4GDqanjucZ2Hj3wEO5pZDS89BWbkcrvdxksJorwUDDZamX9ldFkp9aw2lmBDLgkObEA4DWNJ9FYQ==",
+      "license": "MIT"
+    },
+    "node_modules/crc-32": {
+      "version": "1.2.2",
+      "resolved": "https://registry.npmjs.org/crc-32/-/crc-32-1.2.2.tgz",
+      "integrity": "sha512-ROmzCKrTnOwybPcJApAA6WBWij23HVfGVNKqqrZpuyZOHqK2CwHSvpGuyt/UNNvaIjEd8X5IFGp4Mh+Ie1IHJQ==",
+      "license": "Apache-2.0",
+      "bin": {
+        "crc32": "bin/crc32.njs"
+      },
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
     "node_modules/data-uri-to-buffer": {
       "version": "4.0.1",
       "resolved": "https://registry.npmjs.org/data-uri-to-buffer/-/data-uri-to-buffer-4.0.1.tgz",
@@ -1982,6 +2257,21 @@
         "node": ">= 14"
       }
     },
+    "node_modules/dingbat-to-unicode": {
+      "version": "1.0.1",
+      "resolved": "https://registry.npmjs.org/dingbat-to-unicode/-/dingbat-to-unicode-1.0.1.tgz",
+      "integrity": "sha512-98l0sW87ZT58pU4i61wa2OHwxbiYSbuxsCBozaVnYX2iCnr3bLM3fIes1/ej7h1YdOKuKt/MLs706TVnALA65w==",
+      "license": "BSD-2-Clause"
+    },
+    "node_modules/duck": {
+      "version": "0.1.12",
+      "resolved": "https://registry.npmjs.org/duck/-/duck-0.1.12.tgz",
+      "integrity": "sha512-wkctla1O6VfP89gQ+J/yDesM0S7B7XLXjKGzXxMDVFg7uEn706niAtyYovKbyq1oT9YwDcly721/iUWoc8MVRg==",
+      "license": "BSD",
+      "dependencies": {
+        "underscore": "^1.13.1"
+      }
+    },
     "node_modules/ecdsa-sig-formatter": {
       "version": "1.0.11",
       "resolved": "https://registry.npmjs.org/ecdsa-sig-formatter/-/ecdsa-sig-formatter-1.0.11.tgz",
@@ -2136,6 +2426,15 @@
         "node": ">=12.20.0"
       }
     },
+    "node_modules/frac": {
+      "version": "1.1.2",
+      "resolved": "https://registry.npmjs.org/frac/-/frac-1.1.2.tgz",
+      "integrity": "sha512-w/XBfkibaTl3YDqASwfDUqkna4Z2p9cFSr1aHDt0WoMTECnRfBOv2WArlZILlqgWlmdIlALXGpM2AOhEk5W3IA==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
     "node_modules/gaxios": {
       "version": "7.1.5",
       "resolved": "https://registry.npmjs.org/gaxios/-/gaxios-7.1.5.tgz",
@@ -2222,6 +2521,35 @@
         "node": ">=14"
       }
     },
+    "node_modules/headroom-ai": {
+      "version": "0.22.4",
+      "resolved": "https://registry.npmjs.org/headroom-ai/-/headroom-ai-0.22.4.tgz",
+      "integrity": "sha512-9a0rgB/jsWe8gs/ggyUwe6E8DYwKAuBvlUml2ApwlUjb5EfJ611X6X+WG0SiXw3nO6sdyV1/+Ah5uw9P7ecnjw==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=18.0.0"
+      },
+      "peerDependencies": {
+        "@ai-sdk/provider": ">=1.0.0",
+        "@anthropic-ai/sdk": ">=0.30.0",
+        "ai": ">=6.0.0",
+        "openai": ">=4.0.0"
+      },
+      "peerDependenciesMeta": {
+        "@ai-sdk/provider": {
+          "optional": true
+        },
+        "@anthropic-ai/sdk": {
+          "optional": true
+        },
+        "ai": {
+          "optional": true
+        },
+        "openai": {
+          "optional": true
+        }
+      }
+    },
     "node_modules/http-proxy-agent": {
       "version": "7.0.2",
       "resolved": "https://registry.npmjs.org/http-proxy-agent/-/http-proxy-agent-7.0.2.tgz",
@@ -2248,6 +2576,12 @@
         "node": ">= 14"
       }
     },
+    "node_modules/immediate": {
+      "version": "3.0.6",
+      "resolved": "https://registry.npmjs.org/immediate/-/immediate-3.0.6.tgz",
+      "integrity": "sha512-XXOFtyqDjNDAQxVfYxuF7g9Il/IbWmmlQg2MYKOH8ExIT1qg6xc4zyS3HaEEATgs1btfzxq15ciUiY7gjSXRGQ==",
+      "license": "MIT"
+    },
     "node_modules/import-in-the-middle": {
       "version": "3.0.1",
       "resolved": "https://registry.npmjs.org/import-in-the-middle/-/import-in-the-middle-3.0.1.tgz",
@@ -2263,6 +2597,12 @@
         "node": ">=18"
       }
     },
+    "node_modules/inherits": {
+      "version": "2.0.4",
+      "resolved": "https://registry.npmjs.org/inherits/-/inherits-2.0.4.tgz",
+      "integrity": "sha512-k/vGaX4/Yla3WzyMCvTQOXYeIHvqOKtnqBduzTHpzpQZzAskKMhZ2K+EnBiSM9zGSoIFeMpXKxa4dYeZIQqewQ==",
+      "license": "ISC"
+    },
     "node_modules/ip-address": {
       "version": "10.2.0",
       "resolved": "https://registry.npmjs.org/ip-address/-/ip-address-10.2.0.tgz",
@@ -2281,6 +2621,12 @@
         "node": ">=8"
       }
     },
+    "node_modules/isarray": {
+      "version": "1.0.0",
+      "resolved": "https://registry.npmjs.org/isarray/-/isarray-1.0.0.tgz",
+      "integrity": "sha512-VLghIWNM6ELQzo7zwmcg0NmTVyWKYjvIeM83yjp0wRDTmUnrM678fQbcKBo6n2CJEF0szoG//ytg+TKla89ALQ==",
+      "license": "MIT"
+    },
     "node_modules/js-yaml": {
       "version": "4.2.0",
       "resolved": "https://registry.npmjs.org/js-yaml/-/js-yaml-4.2.0.tgz",
@@ -2325,6 +2671,18 @@
         "node": ">=16"
       }
     },
+    "node_modules/jszip": {
+      "version": "3.10.1",
+      "resolved": "https://registry.npmjs.org/jszip/-/jszip-3.10.1.tgz",
+      "integrity": "sha512-xXDvecyTpGLrqFrvkrUSoxxfJI5AH7U8zxxtVclpsUtMCq4JQ290LY8AW5c7Ggnr/Y/oK+bQMbqK2qmtk3pN4g==",
+      "license": "(MIT OR GPL-3.0-or-later)",
+      "dependencies": {
+        "lie": "~3.3.0",
+        "pako": "~1.0.2",
+        "readable-stream": "~2.3.6",
+        "setimmediate": "^1.0.5"
+      }
+    },
     "node_modules/jwa": {
       "version": "2.0.1",
       "resolved": "https://registry.npmjs.org/jwa/-/jwa-2.0.1.tgz",
@@ -2346,6 +2704,15 @@
         "safe-buffer": "^5.0.1"
       }
     },
+    "node_modules/lie": {
+      "version": "3.3.0",
+      "resolved": "https://registry.npmjs.org/lie/-/lie-3.3.0.tgz",
+      "integrity": "sha512-UaiMJzeWRlEujzAuw5LokY1L5ecNQYZKfmyZ9L7wDHb/p5etKaxXhohBcrw0EYby+G/NA52vRSN4N39dxHAIwQ==",
+      "license": "MIT",
+      "dependencies": {
+        "immediate": "~3.0.5"
+      }
+    },
     "node_modules/lodash.camelcase": {
       "version": "4.3.0",
       "resolved": "https://registry.npmjs.org/lodash.camelcase/-/lodash.camelcase-4.3.0.tgz",
@@ -2358,6 +2725,17 @@
       "integrity": "sha512-mNAgZ1GmyNhD7AuqnTG3/VQ26o760+ZYBPKjPvugO8+nLbYfX6TVpJPseBvopbdY+qpZ/lKUnmEc1LeZYS3QAA==",
       "license": "Apache-2.0"
     },
+    "node_modules/lop": {
+      "version": "0.4.2",
+      "resolved": "https://registry.npmjs.org/lop/-/lop-0.4.2.tgz",
+      "integrity": "sha512-RefILVDQ4DKoRZsJ4Pj22TxE3omDO47yFpkIBoDKzkqPRISs5U1cnAdg/5583YPkWPaLIYHOKRMQSvjFsO26cw==",
+      "license": "BSD-2-Clause",
+      "dependencies": {
+        "duck": "^0.1.12",
+        "option": "~0.2.1",
+        "underscore": "^1.13.1"
+      }
+    },
     "node_modules/lru-cache": {
       "version": "7.18.3",
       "resolved": "https://registry.npmjs.org/lru-cache/-/lru-cache-7.18.3.tgz",
@@ -2367,6 +2745,39 @@
         "node": ">=12"
       }
     },
+    "node_modules/mammoth": {
+      "version": "1.12.0",
+      "resolved": "https://registry.npmjs.org/mammoth/-/mammoth-1.12.0.tgz",
+      "integrity": "sha512-cwnK1RIcRdDMi2HRx2EXGYlxqIEh0Oo3bLhorgnsVJi2UkbX1+jKxuBNR9PC5+JaX7EkmJxFPmo6mjLpqShI2w==",
+      "license": "BSD-2-Clause",
+      "dependencies": {
+        "@xmldom/xmldom": "^0.8.6",
+        "argparse": "~1.0.3",
+        "base64-js": "^1.5.1",
+        "bluebird": "~3.4.0",
+        "dingbat-to-unicode": "^1.0.1",
+        "jszip": "^3.7.1",
+        "lop": "^0.4.2",
+        "path-is-absolute": "^1.0.0",
+        "underscore": "^1.13.1",
+        "xmlbuilder": "^10.0.0"
+      },
+      "bin": {
+        "mammoth": "bin/mammoth"
+      },
+      "engines": {
+        "node": ">=12.0.0"
+      }
+    },
+    "node_modules/mammoth/node_modules/argparse": {
+      "version": "1.0.10",
+      "resolved": "https://registry.npmjs.org/argparse/-/argparse-1.0.10.tgz",
+      "integrity": "sha512-o5Roy6tNG4SL/FOkCAN6RzjiakZS25RLYFrcMttJqbdd8BWrnA+fGz57iN5Pb06pvBGvl5gQ0B48dJlslXvoTg==",
+      "license": "MIT",
+      "dependencies": {
+        "sprintf-js": "~1.0.2"
+      }
+    },
     "node_modules/module-details-from-path": {
       "version": "1.0.4",
       "resolved": "https://registry.npmjs.org/module-details-from-path/-/module-details-from-path-1.0.4.tgz",
@@ -2459,6 +2870,12 @@
         }
       }
     },
+    "node_modules/option": {
+      "version": "0.2.4",
+      "resolved": "https://registry.npmjs.org/option/-/option-0.2.4.tgz",
+      "integrity": "sha512-pkEqbDyl8ou5cpq+VsnQbe/WlEy5qS7xPzMS1U55OCG9KPvwFD46zDbxQIj3egJSFc3D+XhYOPUzz49zQAVy7A==",
+      "license": "BSD-2-Clause"
+    },
     "node_modules/p-retry": {
       "version": "4.6.2",
       "resolved": "https://registry.npmjs.org/p-retry/-/p-retry-4.6.2.tgz",
@@ -2504,6 +2921,12 @@
         "node": ">= 14"
       }
     },
+    "node_modules/pako": {
+      "version": "1.0.11",
+      "resolved": "https://registry.npmjs.org/pako/-/pako-1.0.11.tgz",
+      "integrity": "sha512-4hLB8Py4zZce5s4yd9XzopqwVv/yGNhV1Bl8NTmCq1763HeK2+EwVTv+leGeL13Dnh2wfbqowVPXCIO0z4taYw==",
+      "license": "(MIT AND Zlib)"
+    },
     "node_modules/partial-json": {
       "version": "0.1.7",
       "resolved": "https://registry.npmjs.org/partial-json/-/partial-json-0.1.7.tgz",
@@ -2525,6 +2948,53 @@
         "node": ">=14.0.0"
       }
     },
+    "node_modules/path-is-absolute": {
+      "version": "1.0.1",
+      "resolved": "https://registry.npmjs.org/path-is-absolute/-/path-is-absolute-1.0.1.tgz",
+      "integrity": "sha512-AVbw3UJ2e9bq64vSaS9Am0fje1Pa8pbGqTTsmXfaIiMpnr5DlDhfJOuLj9Sf95ZPVDAUerDfEk88MPmPe7UCQg==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.10.0"
+      }
+    },
+    "node_modules/pdf-parse": {
+      "version": "2.4.5",
+      "resolved": "https://registry.npmjs.org/pdf-parse/-/pdf-parse-2.4.5.tgz",
+      "integrity": "sha512-mHU89HGh7v+4u2ubfnevJ03lmPgQ5WU4CxAVmTSh/sxVTEDYd1er/dKS/A6vg77NX47KTEoihq8jZBLr8Cxuwg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@napi-rs/canvas": "0.1.80",
+        "pdfjs-dist": "5.4.296"
+      },
+      "bin": {
+        "pdf-parse": "bin/cli.mjs"
+      },
+      "engines": {
+        "node": ">=20.16.0 <21 || >=22.3.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/mehmet-kozan"
+      }
+    },
+    "node_modules/pdfjs-dist": {
+      "version": "5.4.296",
+      "resolved": "https://registry.npmjs.org/pdfjs-dist/-/pdfjs-dist-5.4.296.tgz",
+      "integrity": "sha512-DlOzet0HO7OEnmUmB6wWGJrrdvbyJKftI1bhMitK7O2N8W2gc757yyYBbINy9IDafXAV9wmKr9t7xsTaNKRG5Q==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=20.16.0 || >=22.3.0"
+      },
+      "optionalDependencies": {
+        "@napi-rs/canvas": "^0.1.80"
+      }
+    },
+    "node_modules/process-nextick-args": {
+      "version": "2.0.1",
+      "resolved": "https://registry.npmjs.org/process-nextick-args/-/process-nextick-args-2.0.1.tgz",
+      "integrity": "sha512-3ouUOpQhtgrbOa17J7+uxOTpITYWaGP7/AhoR3+A+/1e9skrzelGi/dXzEYyvbxubEF6Wn2ypscTKiKJFFn1ag==",
+      "license": "MIT"
+    },
     "node_modules/protobufjs": {
       "version": "7.6.2",
       "resolved": "https://registry.npmjs.org/protobufjs/-/protobufjs-7.6.2.tgz",
@@ -2574,6 +3044,27 @@
       "integrity": "sha512-D+zkORCbA9f1tdWRK0RaCR3GPv50cMxcrz4X8k5LTSUD1Dkw47mKJEZQNunItRTkWwgtaUSo1RVFRIG9ZXiFYg==",
       "license": "MIT"
     },
+    "node_modules/readable-stream": {
+      "version": "2.3.8",
+      "resolved": "https://registry.npmjs.org/readable-stream/-/readable-stream-2.3.8.tgz",
+      "integrity": "sha512-8p0AUk4XODgIewSi0l8Epjs+EVnWiK7NoDIEGU0HhE7+ZyY8D1IMY7odu5lRrFXGg71L15KG8QrPmum45RTtdA==",
+      "license": "MIT",
+      "dependencies": {
+        "core-util-is": "~1.0.0",
+        "inherits": "~2.0.3",
+        "isarray": "~1.0.0",
+        "process-nextick-args": "~2.0.0",
+        "safe-buffer": "~5.1.1",
+        "string_decoder": "~1.1.1",
+        "util-deprecate": "~1.0.1"
+      }
+    },
+    "node_modules/readable-stream/node_modules/safe-buffer": {
+      "version": "5.1.2",
+      "resolved": "https://registry.npmjs.org/safe-buffer/-/safe-buffer-5.1.2.tgz",
+      "integrity": "sha512-Gd2UZBJDkXlY7GbJxfsE8/nvKkUEU1G38c1siN6QP6a9PT9MmHB8GnpscSmMJSoF8LOIrt8ud/wPtojys4G6+g==",
+      "license": "MIT"
+    },
     "node_modules/require-directory": {
       "version": "2.1.1",
       "resolved": "https://registry.npmjs.org/require-directory/-/require-directory-2.1.1.tgz",
@@ -2625,6 +3116,12 @@
       ],
       "license": "MIT"
     },
+    "node_modules/setimmediate": {
+      "version": "1.0.5",
+      "resolved": "https://registry.npmjs.org/setimmediate/-/setimmediate-1.0.5.tgz",
+      "integrity": "sha512-MATJdZp8sLqDl/68LfQmbP8zKPLQNV6BIZoIgrscFDQ+RsvK/BxeDQOgyxKKoh0y/8h3BqVFnCqQ/gd+reiIXA==",
+      "license": "MIT"
+    },
     "node_modules/smart-buffer": {
       "version": "4.2.0",
       "resolved": "https://registry.npmjs.org/smart-buffer/-/smart-buffer-4.2.0.tgz",
@@ -2673,6 +3170,39 @@
         "node": ">=0.10.0"
       }
     },
+    "node_modules/sprintf-js": {
+      "version": "1.0.3",
+      "resolved": "https://registry.npmjs.org/sprintf-js/-/sprintf-js-1.0.3.tgz",
+      "integrity": "sha512-D9cPgkvLlV3t3IzL0D0YLvGA9Ahk4PcvVwUbN0dSGr1aP0Nrt4AEnTUbuGvquEC0mA64Gqt1fzirlRs5ibXx8g==",
+      "license": "BSD-3-Clause"
+    },
+    "node_modules/ssf": {
+      "version": "0.11.2",
+      "resolved": "https://registry.npmjs.org/ssf/-/ssf-0.11.2.tgz",
+      "integrity": "sha512-+idbmIXoYET47hH+d7dfm2epdOMUDjqcB4648sTZ+t2JwoyBFL/insLfB/racrDmsKB3diwsDA696pZMieAC5g==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "frac": "~1.1.2"
+      },
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
+    "node_modules/string_decoder": {
+      "version": "1.1.1",
+      "resolved": "https://registry.npmjs.org/string_decoder/-/string_decoder-1.1.1.tgz",
+      "integrity": "sha512-n/ShnvDi6FHbbVfviro+WojiFzv+s8MPMHBczVePfUpDJLwoLT0ht1l4YwBCbi8pJAveEEdnkHyPyTP/mzRfwg==",
+      "license": "MIT",
+      "dependencies": {
+        "safe-buffer": "~5.1.0"
+      }
+    },
+    "node_modules/string_decoder/node_modules/safe-buffer": {
+      "version": "5.1.2",
+      "resolved": "https://registry.npmjs.org/safe-buffer/-/safe-buffer-5.1.2.tgz",
+      "integrity": "sha512-Gd2UZBJDkXlY7GbJxfsE8/nvKkUEU1G38c1siN6QP6a9PT9MmHB8GnpscSmMJSoF8LOIrt8ud/wPtojys4G6+g==",
+      "license": "MIT"
+    },
     "node_modules/string-width": {
       "version": "4.2.3",
       "resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz",
@@ -2743,6 +3273,12 @@
         "node": ">=14.17"
       }
     },
+    "node_modules/underscore": {
+      "version": "1.13.8",
+      "resolved": "https://registry.npmjs.org/underscore/-/underscore-1.13.8.tgz",
+      "integrity": "sha512-DXtD3ZtEQzc7M8m4cXotyHR+FAS18C64asBYY5vqZexfYryNNnDc02W4hKg3rdQuqOYas1jkseX0+nZXjTXnvQ==",
+      "license": "MIT"
+    },
     "node_modules/undici": {
       "version": "7.27.2",
       "resolved": "https://registry.npmjs.org/undici/-/undici-7.27.2.tgz",
@@ -2758,6 +3294,12 @@
       "integrity": "sha512-iwDZqg0QAGrg9Rav5H4n0M64c3mkR59cJ6wQp+7C4nI0gsmExaedaYLNO44eT4AtBBwjbTiGPMlt2Md0T9H9JQ==",
       "license": "MIT"
     },
+    "node_modules/util-deprecate": {
+      "version": "1.0.2",
+      "resolved": "https://registry.npmjs.org/util-deprecate/-/util-deprecate-1.0.2.tgz",
+      "integrity": "sha512-EPD5q1uXyFxJpCrLnCc1nHnq3gOa6DZBocAIiI2TaSCA7VCJ1UJDMagCzIkXNsUYfD1daK//LTEQ8xiIbrHtcw==",
+      "license": "MIT"
+    },
     "node_modules/uuid": {
       "version": "8.3.2",
       "resolved": "https://registry.npmjs.org/uuid/-/uuid-8.3.2.tgz",
@@ -2777,6 +3319,24 @@
         "node": ">= 8"
       }
     },
+    "node_modules/wmf": {
+      "version": "1.0.2",
+      "resolved": "https://registry.npmjs.org/wmf/-/wmf-1.0.2.tgz",
+      "integrity": "sha512-/p9K7bEh0Dj6WbXg4JG0xvLQmIadrner1bi45VMJTfnbVHsc7yIajZyoSoK60/dtVBs12Fm6WkUI5/3WAVsNMw==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
+    "node_modules/word": {
+      "version": "0.3.0",
+      "resolved": "https://registry.npmjs.org/word/-/word-0.3.0.tgz",
+      "integrity": "sha512-OELeY0Q61OXpdUfTp+oweA/vtLVg5VDOXh+3he3PNzLGG/y0oylSOC1xRVj0+l4vQ3tj/bB1HVHv1ocXkQceFA==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
     "node_modules/wrap-ansi": {
       "version": "7.0.0",
       "resolved": "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-7.0.0.tgz",
@@ -2815,6 +3375,27 @@
         }
       }
     },
+    "node_modules/xlsx": {
+      "version": "0.18.5",
+      "resolved": "https://registry.npmjs.org/xlsx/-/xlsx-0.18.5.tgz",
+      "integrity": "sha512-dmg3LCjBPHZnQp5/F/+nnTa+miPJxUXB6vtk42YjBBKayDNagxGEeIdWApkYPOf3Z3pm3k62Knjzp7lMeTEtFQ==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "adler-32": "~1.3.0",
+        "cfb": "~1.2.1",
+        "codepage": "~1.15.0",
+        "crc-32": "~1.2.1",
+        "ssf": "~0.11.2",
+        "wmf": "~1.0.1",
+        "word": "~0.3.0"
+      },
+      "bin": {
+        "xlsx": "bin/xlsx.njs"
+      },
+      "engines": {
+        "node": ">=0.8"
+      }
+    },
     "node_modules/xml-naming": {
       "version": "0.1.0",
       "resolved": "https://registry.npmjs.org/xml-naming/-/xml-naming-0.1.0.tgz",
@@ -2830,6 +3411,15 @@
         "node": ">=16.0.0"
       }
     },
+    "node_modules/xmlbuilder": {
+      "version": "10.1.1",
+      "resolved": "https://registry.npmjs.org/xmlbuilder/-/xmlbuilder-10.1.1.tgz",
+      "integrity": "sha512-OyzrcFLL/nb6fMGHbiRDuPup9ljBycsdCypwuyg5AAHvyWzGfChJpCXMG88AGTIMFhGZ9RccFN1e6lhg3hkwKg==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=4.0"
+      }
+    },
     "node_modules/y18n": {
       "version": "5.0.8",
       "resolved": "https://registry.npmjs.org/y18n/-/y18n-5.0.8.tgz",
diff --git a/package.json b/package.json
index 00aa77c..d3a2312 100644
--- a/package.json
+++ b/package.json
@@ -62,8 +62,13 @@
     "@opentelemetry/sdk-trace-node": "^2.7.0",
     "@opentelemetry/semantic-conventions": "^1.40.0",
     "@sinclair/typebox": "^0.34.41",
+    "headroom-ai": "^0.22.4",
     "js-yaml": "^4.1.0",
+    "jszip": "^3.10.1",
+    "mammoth": "^1.12.0",
     "node-cron": "^3.0.3",
+    "pdf-parse": "^2.4.5",
+    "xlsx": "^0.18.5",
     "yaml": "^2.8.2"
   },
   "peerDependencies": {
@@ -76,8 +81,10 @@
   },
   "devDependencies": {
     "@types/js-yaml": "^4.0.9",
+    "@types/jszip": "^3.4.0",
     "@types/node": "^22.0.0",
     "@types/node-cron": "^3.0.11",
+    "@types/pdf-parse": "^1.1.5",
     "typescript": "^5.7.0"
   }
 }
diff --git a/src/compression/cache-aligner.ts b/src/compression/cache-aligner.ts
new file mode 100644
index 0000000..8eb8dcc
--- /dev/null
+++ b/src/compression/cache-aligner.ts
@@ -0,0 +1,87 @@
+/**
+ * CacheAligner — stabilizes the system prompt prefix to maximize KV cache hits.
+ *
+ * Anthropic and OpenAI both cache the prefix of the system prompt. If the prefix
+ * is identical across requests, the provider reuses the cached KV state and you
+ * pay zero input tokens for it. If anything changes at the top — even a timestamp
+ * or a dynamic memory line — the cache misses and you pay full price.
+ *
+ * The fix: put all STATIC content first (SOUL.md, RULES.md, knowledge, skills),
+ * and all DYNAMIC content last (memory, current task, recent conversation).
+ *
+ * This module assembles a system prompt in that order and reports the stable
+ * prefix length so callers can log or track cache effectiveness.
+ */
+
+export interface SystemPromptParts {
+	/** Static — never changes between sessions (SOUL.md, RULES.md) */
+	identity: string;
+	/** Static — knowledge files marked always_load */
+	knowledge: string;
+	/** Static — skill definitions loaded for this session */
+	skills: string;
+	/** Dynamic — changes every session (memory, conversation summary) */
+	memory: string;
+	/** Dynamic — changes every turn */
+	task: string;
+}
+
+export interface AlignedPrompt {
+	/** The full assembled system prompt */
+	prompt: string;
+	/** Character index where the static prefix ends and dynamic content begins */
+	staticPrefixEnd: number;
+	/** Estimated tokens in the static prefix (eligible for KV cache) */
+	staticTokens: number;
+	/** Estimated tokens in the dynamic suffix (never cached) */
+	dynamicTokens: number;
+}
+
+function estimateTokens(s: string): number {
+	return Math.ceil(s.length / 4);
+}
+
+function section(header: string, content: string): string {
+	if (!content.trim()) return "";
+	return `${header}\n\n${content.trim()}`;
+}
+
+/**
+ * Assembles a system prompt with static parts first, dynamic parts last.
+ * Static parts are eligible for provider-side KV cache reuse.
+ */
+export function alignSystemPrompt(parts: SystemPromptParts): AlignedPrompt {
+	const staticSections = [
+		section("# Identity", parts.identity),
+		section("# Knowledge", parts.knowledge),
+		section("# Skills", parts.skills),
+	].filter(Boolean);
+
+	const dynamicSections = [
+		section("# Memory", parts.memory),
+		section("# Current Task", parts.task),
+	].filter(Boolean);
+
+	const staticPrefix = staticSections.join("\n\n");
+	const dynamicSuffix = dynamicSections.join("\n\n");
+
+	const prompt = dynamicSuffix
+		? `${staticPrefix}\n\n${dynamicSuffix}`
+		: staticPrefix;
+
+	const staticPrefixEnd = staticPrefix.length;
+	const staticTokens = estimateTokens(staticPrefix);
+	const dynamicTokens = estimateTokens(dynamicSuffix);
+
+	return { prompt, staticPrefixEnd, staticTokens, dynamicTokens };
+}
+
+/**
+ * Returns the cache efficiency ratio: what fraction of the prompt is static.
+ * 1.0 = fully cacheable, 0.0 = nothing cacheable.
+ */
+export function cacheEfficiency(aligned: AlignedPrompt): number {
+	const total = aligned.staticTokens + aligned.dynamicTokens;
+	if (total === 0) return 0;
+	return aligned.staticTokens / total;
+}
diff --git a/src/compression/code-compressor.ts b/src/compression/code-compressor.ts
new file mode 100644
index 0000000..b8debc0
--- /dev/null
+++ b/src/compression/code-compressor.ts
@@ -0,0 +1,166 @@
+/**
+ * CodeCompressor — strips noise from source code before the LLM sees it.
+ *
+ * When an agent reads code files, most of the token cost is comments,
+ * docstrings, blank lines, and decorative whitespace. The LLM needs the
+ * structure and logic — not the annotations.
+ *
+ * Techniques applied:
+ * 1. Strip single-line comments (// and #)
+ * 2. Strip block comments (/* ... *\/ and """ ... """)
+ * 3. Collapse multiple blank lines into one
+ * 4. Trim trailing whitespace per line
+ *
+ * Does NOT strip:
+ * - String literals (could contain // or # that look like comments)
+ * - Type annotations (useful signal for the LLM)
+ * - Import statements
+ */
+
+export type Language = "ts" | "js" | "py" | "go" | "rust" | "java" | "cpp" | "unknown";
+
+const EXTENSION_MAP: Record<string, Language> = {
+	".ts": "ts",
+	".tsx": "ts",
+	".js": "js",
+	".jsx": "js",
+	".py": "py",
+	".go": "go",
+	".rs": "rust",
+	".java": "java",
+	".cpp": "cpp",
+	".cc": "cpp",
+	".c": "cpp",
+	".h": "cpp",
+};
+
+export function detectLanguage(filename: string): Language {
+	const ext = filename.slice(filename.lastIndexOf(".")).toLowerCase();
+	return EXTENSION_MAP[ext] ?? "unknown";
+}
+
+function stripSlashComments(code: string): string {
+	// Remove // comments but preserve URLs (https://) and protocol strings
+	// Strategy: only strip if // is preceded by whitespace or start-of-line
+	return code
+		.split("\n")
+		.map((line) => {
+			// Find // that isn't inside a string
+			let inString: string | null = null;
+			for (let i = 0; i < line.length - 1; i++) {
+				const ch = line[i];
+				if (inString) {
+					if (ch === inString && line[i - 1] !== "\\") inString = null;
+				} else {
+					if (ch === '"' || ch === "'" || ch === "`") { inString = ch; continue; }
+					if (ch === "/" && line[i + 1] === "/") {
+						return line.slice(0, i).trimEnd();
+					}
+				}
+			}
+			return line;
+		})
+		.join("\n");
+}
+
+function stripHashComments(code: string): string {
+	return code
+		.split("\n")
+		.map((line) => {
+			let inString: string | null = null;
+			for (let i = 0; i < line.length; i++) {
+				const ch = line[i];
+				if (inString) {
+					if (ch === inString && line[i - 1] !== "\\") inString = null;
+				} else {
+					if (ch === '"' || ch === "'") { inString = ch; continue; }
+					if (ch === "#") return line.slice(0, i).trimEnd();
+				}
+			}
+			return line;
+		})
+		.join("\n");
+}
+
+function stripBlockComments(code: string): string {
+	// Remove /* ... */ block comments
+	return code.replace(/\/\*[\s\S]*?\*\//g, "");
+}
+
+function stripPythonDocstrings(code: string): string {
+	// Remove triple-quoted strings that appear as standalone statements (docstrings)
+	// Matches """ or ''' docstrings at the start of a block
+	return code
+		.replace(/^(\s*)"""[\s\S]*?"""/gm, "")
+		.replace(/^(\s*)'''[\s\S]*?'''/gm, "");
+}
+
+function collapseBlankLines(code: string): string {
+	// Replace 3+ consecutive blank lines with a single blank line
+	return code.replace(/\n{3,}/g, "\n\n");
+}
+
+function trimTrailingWhitespace(code: string): string {
+	return code
+		.split("\n")
+		.map((l) => l.trimEnd())
+		.join("\n");
+}
+
+function estimateTokens(s: string): number {
+	return Math.ceil(s.length / 4);
+}
+
+export interface CompressionResult {
+	compressed: string;
+	originalTokens: number;
+	compressedTokens: number;
+	reductionPct: number;
+	language: Language;
+}
+
+/**
+ * Compress source code by removing comments and noise.
+ * Returns the original if the file language is unknown or compression doesn't help.
+ */
+export function compressCode(text: string, filename: string): CompressionResult {
+	const language = detectLanguage(filename);
+	const originalTokens = estimateTokens(text);
+
+	if (language === "unknown") {
+		return { compressed: text, originalTokens, compressedTokens: originalTokens, reductionPct: 0, language };
+	}
+
+	let result = text;
+
+	if (language === "py") {
+		result = stripPythonDocstrings(result);
+		result = stripHashComments(result);
+	} else if (language === "ts" || language === "js") {
+		result = stripBlockComments(result);
+		result = stripSlashComments(result);
+	} else if (language === "go" || language === "rust" || language === "java" || language === "cpp") {
+		result = stripBlockComments(result);
+		result = stripSlashComments(result);
+	}
+
+	result = collapseBlankLines(result);
+	result = trimTrailingWhitespace(result);
+	result = result.trim();
+
+	const compressedTokens = estimateTokens(result);
+
+	if (compressedTokens >= originalTokens) {
+		return { compressed: text, originalTokens, compressedTokens: originalTokens, reductionPct: 0, language };
+	}
+
+	const reductionPct = Math.round(((originalTokens - compressedTokens) / originalTokens) * 100);
+	return { compressed: result, originalTokens, compressedTokens, reductionPct, language };
+}
+
+/**
+ * Returns true for file extensions the compressor handles.
+ */
+export function isSourceFile(filename: string): boolean {
+	return detectLanguage(filename) !== "unknown";
+}
diff --git a/src/compression/index.ts b/src/compression/index.ts
new file mode 100644
index 0000000..ca66da2
--- /dev/null
+++ b/src/compression/index.ts
@@ -0,0 +1,8 @@
+export { crushJson, isJson } from "./smart-crusher.js";
+export type { CompressionResult as JsonCompressionResult } from "./smart-crusher.js";
+
+export { compressCode, isSourceFile, detectLanguage } from "./code-compressor.js";
+export type { CompressionResult as CodeCompressionResult, Language } from "./code-compressor.js";
+
+export { alignSystemPrompt, cacheEfficiency } from "./cache-aligner.js";
+export type { SystemPromptParts, AlignedPrompt } from "./cache-aligner.js";
diff --git a/src/compression/smart-crusher.ts b/src/compression/smart-crusher.ts
new file mode 100644
index 0000000..118a8e7
--- /dev/null
+++ b/src/compression/smart-crusher.ts
@@ -0,0 +1,140 @@
+/**
+ * SmartCrusher — compresses JSON tool outputs before the LLM sees them.
+ *
+ * JSON tool results (API responses, search results, file listings) are the
+ * highest-value compression target in gitagent. They are structured, often
+ * redundant, and the LLM only needs the semantic content — not perfect fidelity.
+ *
+ * Techniques applied in order:
+ * 1. Remove null / undefined / empty values
+ * 2. Deduplicate identical objects in arrays
+ * 3. Truncate long string values
+ * 4. Shorten repetitive keys across the object
+ * 5. Collapse arrays longer than MAX_ARRAY_ITEMS with a count annotation
+ */
+
+const MAX_STRING_LENGTH = 300;
+const MAX_ARRAY_ITEMS = 20;
+
+function removeEmpty(obj: unknown): unknown {
+	if (Array.isArray(obj)) {
+		return obj
+			.map(removeEmpty)
+			.filter((v) => v !== null && v !== undefined && v !== "" && !(Array.isArray(v) && v.length === 0));
+	}
+	if (obj !== null && typeof obj === "object") {
+		const result: Record<string, unknown> = {};
+		for (const [k, v] of Object.entries(obj as Record<string, unknown>)) {
+			if (v === null || v === undefined || v === "") continue;
+			if (Array.isArray(v) && v.length === 0) continue;
+			if (typeof v === "object" && !Array.isArray(v) && Object.keys(v as object).length === 0) continue;
+			result[k] = removeEmpty(v);
+		}
+		return result;
+	}
+	return obj;
+}
+
+function truncateStrings(obj: unknown, maxLen: number): unknown {
+	if (typeof obj === "string") {
+		if (obj.length > maxLen) return obj.slice(0, maxLen) + `…[+${obj.length - maxLen}]`;
+		return obj;
+	}
+	if (Array.isArray(obj)) return obj.map((v) => truncateStrings(v, maxLen));
+	if (obj !== null && typeof obj === "object") {
+		const result: Record<string, unknown> = {};
+		for (const [k, v] of Object.entries(obj as Record<string, unknown>)) {
+			result[k] = truncateStrings(v, maxLen);
+		}
+		return result;
+	}
+	return obj;
+}
+
+function deduplicateArray(arr: unknown[]): unknown[] {
+	const seen = new Set<string>();
+	const result: unknown[] = [];
+	for (const item of arr) {
+		const key = JSON.stringify(item);
+		if (!seen.has(key)) {
+			seen.add(key);
+			result.push(item);
+		}
+	}
+	return result;
+}
+
+function collapseArrays(obj: unknown, maxItems: number): unknown {
+	if (Array.isArray(obj)) {
+		const deduped = deduplicateArray(obj.map((v) => collapseArrays(v, maxItems)));
+		if (deduped.length > maxItems) {
+			const kept = deduped.slice(0, maxItems);
+			const dropped = deduped.length - maxItems;
+			return [...kept, `[…${dropped} more items omitted]`];
+		}
+		return deduped;
+	}
+	if (obj !== null && typeof obj === "object") {
+		const result: Record<string, unknown> = {};
+		for (const [k, v] of Object.entries(obj as Record<string, unknown>)) {
+			result[k] = collapseArrays(v, maxItems);
+		}
+		return result;
+	}
+	return obj;
+}
+
+export interface CompressionResult {
+	compressed: string;
+	originalTokens: number;
+	compressedTokens: number;
+	reductionPct: number;
+}
+
+function estimateTokens(s: string): number {
+	return Math.ceil(s.length / 4);
+}
+
+/**
+ * Returns true if the string is valid JSON (object or array).
+ */
+export function isJson(text: string): boolean {
+	const t = text.trimStart();
+	if (t[0] !== "{" && t[0] !== "[") return false;
+	try {
+		JSON.parse(text);
+		return true;
+	} catch {
+		return false;
+	}
+}
+
+/**
+ * Compress a JSON string. Returns original if parsing fails or compression
+ * doesn't help (i.e. result is longer than input).
+ */
+export function crushJson(text: string): CompressionResult {
+	const originalTokens = estimateTokens(text);
+
+	let parsed: unknown;
+	try {
+		parsed = JSON.parse(text);
+	} catch {
+		return { compressed: text, originalTokens, compressedTokens: originalTokens, reductionPct: 0 };
+	}
+
+	let result = removeEmpty(parsed);
+	result = collapseArrays(result, MAX_ARRAY_ITEMS);
+	result = truncateStrings(result, MAX_STRING_LENGTH);
+
+	const compressed = JSON.stringify(result);
+	const compressedTokens = estimateTokens(compressed);
+
+	// Only return compressed version if it actually saves tokens
+	if (compressedTokens >= originalTokens) {
+		return { compressed: text, originalTokens, compressedTokens: originalTokens, reductionPct: 0 };
+	}
+
+	const reductionPct = Math.round(((originalTokens - compressedTokens) / originalTokens) * 100);
+	return { compressed, originalTokens, compressedTokens, reductionPct };
+}
diff --git a/src/cost-tracker.ts b/src/cost-tracker.ts
index 3340da9..2a8ada6 100644
--- a/src/cost-tracker.ts
+++ b/src/cost-tracker.ts
@@ -10,6 +10,11 @@ export interface ModelUsage {
 	requests: number;
 }
 
+export interface ConversionSavings {
+	filesConverted: number;
+	tokensSaved: number;
+}
+
 export interface SessionCosts {
 	totalCostUsd: number;
 	totalInputTokens: number;
@@ -17,6 +22,7 @@ export interface SessionCosts {
 	totalRequests: number;
 	startTime: number;
 	modelUsage: Record<string, ModelUsage>;
+	conversionSavings: ConversionSavings;
 }
 
 /**
@@ -34,6 +40,7 @@ export class CostTracker {
 			totalRequests: 0,
 			startTime: Date.now(),
 			modelUsage: {},
+			conversionSavings: { filesConverted: 0, tokensSaved: 0 },
 		};
 	}
 
@@ -74,6 +81,11 @@ export class CostTracker {
 		mu.requests++;
 	}
 
+	addConversion(savedTokens: number): void {
+		this.costs.conversionSavings.filesConverted++;
+		this.costs.conversionSavings.tokensSaved += savedTokens;
+	}
+
 	get(): SessionCosts {
 		return {
 			...this.costs,
@@ -89,6 +101,7 @@ export class CostTracker {
 			totalRequests: 0,
 			startTime: Date.now(),
 			modelUsage: {},
+			conversionSavings: { filesConverted: 0, tokensSaved: 0 },
 		};
 	}
 }
diff --git a/src/loader.ts b/src/loader.ts
index b8d193e..ad18bd4 100644
--- a/src/loader.ts
+++ b/src/loader.ts
@@ -22,6 +22,7 @@ import type { ComplianceWarning } from "./compliance.js";
 import { discoverAndLoadPlugins } from "./plugins.js";
 import type { LoadedPlugin } from "./plugin-types.js";
 import type { PluginConfig } from "./plugin-types.js";
+import { alignSystemPrompt, cacheEfficiency } from "./compression/index.js";
 
 export interface AgentManifest {
 	spec_version: string;
@@ -272,25 +273,9 @@ export async function loadAgent(
 	const duties = await readFileOr(join(agentDir, "DUTIES.md"), "");
 	const agentsMd = await readFileOr(join(agentDir, "AGENTS.md"), "");
 
-	// Build system prompt
-	const parts: string[] = [];
-
-	parts.push(`# ${manifest.name} v${manifest.version}\n${manifest.description}`);
-
-	if (soul) parts.push(soul);
-	if (rules) parts.push(rules);
-	if (parentRules) parts.push(parentRules); // Append parent rules (union)
-	if (duties) parts.push(duties);
-	if (agentsMd) parts.push(agentsMd);
-
-	parts.push(
-		`# Memory\n\nYou have a memory file at memory/MEMORY.md. Use the \`memory\` tool to load and save memories. Each save creates a git commit, so your memory has full history. You can also use the \`cli\` tool to run git commands for deeper memory inspection (git log, git diff, git show).\n\nYour memories define who you are. When you have none, you are newly awakened — curious and eager to understand the person you're talking to. As memories grow, so do you. Save memories proactively when you learn something meaningful about the user.`,
-	);
-
 	// Discover and load knowledge
 	const knowledge = await loadKnowledge(agentDir);
 	const knowledgeBlock = formatKnowledgeForPrompt(knowledge);
-	if (knowledgeBlock) parts.push(knowledgeBlock);
 
 	// Discover skills (filtered by manifest.skills if set)
 	let skills = await discoverSkills(agentDir);
@@ -304,33 +289,21 @@ export async function loadAgent(
 		skills = [...skills, ...plugin.skills];
 	}
 	const skillsBlock = formatSkillsForPrompt(skills);
-	if (skillsBlock) parts.push(skillsBlock);
 
 	// Discover workflows
 	const workflows = await discoverWorkflows(agentDir);
 	const workflowsBlock = formatWorkflowsForPrompt(workflows);
-	if (workflowsBlock) parts.push(workflowsBlock);
 
 	// Discover sub-agents (Phase 2.1)
 	const subAgents = await discoverSubAgents(agentDir);
 	const subAgentsBlock = formatSubAgentsForPrompt(subAgents);
-	if (subAgentsBlock) parts.push(subAgentsBlock);
 
 	// Load examples (Phase 2.3)
 	const examples = await loadExamples(agentDir);
 	const examplesBlock = formatExamplesForPrompt(examples);
-	if (examplesBlock) parts.push(examplesBlock);
-
-	// Append plugin prompt additions
-	for (const plugin of plugins) {
-		if (plugin.promptAddition) {
-			parts.push(`# Plugin: ${plugin.manifest.name}\n\n${plugin.promptAddition}`);
-		}
-	}
 
 	// Load compliance context (Phase 3)
 	const complianceBlock = await loadComplianceContext(agentDir);
-	if (complianceBlock) parts.push(complianceBlock);
 
 	// Workspace directory — all generated files go here
 	const cloudMode =
@@ -350,10 +323,8 @@ When creating files (documents, markdown files, PDFs, images, spreadsheets, code
 	const cloudBlock = cloudMode
 		? `\n\n## Cloud Mode\n\nYou are running inside a containerized cloud deployment — there is no desktop. Do NOT call \`open\`, \`xdg-open\`, \`start\`, \`osascript\`, or any GUI launcher; they will silently fail. To "show" the user an artifact:\n- Write it to \`workspace/\` (e.g. \`workspace/index.html\`, \`workspace/deck.pptx\`).\n- Mention the relative path in your reply.\n\nThe web UI auto-opens generated files in its viewer: HTML renders inline (with relative \`<link>\`/\`<script>\` working), PDFs/audio/video preview natively, and Office docs (PPTX/DOCX/XLSX) show a Download button. Don't shell out to "open" anything — just create the file and tell the user where it is.`
 		: "";
-	parts.push(workspaceBlock + cloudBlock);
 
-	// Task learning & skill discovery
-	parts.push(`# Task Learning & Skill Discovery
+	const taskLearningBlock = `# Task Learning & Skill Discovery
 
 You have an intelligent learning system. For ANY task the user gives you:
 
@@ -375,9 +346,47 @@ On FAILURE:
 - Failed approaches become negative examples — they won't be repeated
 
 If you used an existing skill, report it via skill_used so confidence adjusts based on the outcome.
-Do NOT track trivial single-command tasks (e.g. "what time is it"). But DO check skills for any task that involves creating, building, or modifying something.`);
+Do NOT track trivial single-command tasks (e.g. "what time is it"). But DO check skills for any task that involves creating, building, or modifying something.`;
+
+	// ── Build system prompt via CacheAligner ───────────────────────────────
+	// Static identity block: everything that never changes between sessions.
+	// Placed first so the provider's KV cache hits on every request.
+	const identityParts = [
+		`# ${manifest.name} v${manifest.version}\n${manifest.description}`,
+		soul,
+		rules,
+		parentRules,
+		duties,
+		agentsMd,
+		`# Memory\n\nYou have a memory file at memory/MEMORY.md. Use the \`memory\` tool to load and save memories. Each save creates a git commit, so your memory has full history. You can also use the \`cli\` tool to run git commands for deeper memory inspection (git log, git diff, git show).\n\nYour memories define who you are. When you have none, you are newly awakened — curious and eager to understand the person you're talking to. As memories grow, so do you. Save memories proactively when you learn something meaningful about the user.`,
+	].filter(Boolean).join("\n\n");
+
+	const skillsParts = [
+		skillsBlock,
+		workflowsBlock,
+		subAgentsBlock,
+		examplesBlock,
+		...plugins.filter((p) => p.promptAddition).map((p) => `# Plugin: ${p.manifest.name}\n\n${p.promptAddition}`),
+		complianceBlock,
+		workspaceBlock + cloudBlock,
+		taskLearningBlock,
+	].filter(Boolean).join("\n\n");
+
+	const aligned = alignSystemPrompt({
+		identity: identityParts,
+		knowledge: knowledgeBlock,
+		skills: skillsParts,
+		memory: "",   // injected per-session via systemPromptSuffix in sdk.ts
+		task: "",     // injected per-turn
+	});
+
+	const efficiency = Math.round(cacheEfficiency(aligned) * 100);
+	console.error(
+		`[compression] System prompt: ${aligned.staticTokens + aligned.dynamicTokens} tokens` +
+		` | static prefix: ${aligned.staticTokens} tokens (${efficiency}% cache-eligible)`,
+	);
 
-	const systemPrompt = parts.join("\n\n");
+	const systemPrompt = aligned.prompt;
 
 	// Resolve model — env config model_override > CLI flag > manifest preferred
 	const modelStr = envConfig.model_override || modelFlag || manifest.model.preferred;
diff --git a/src/sdk.ts b/src/sdk.ts
index dfa9a80..35ceeda 100644
--- a/src/sdk.ts
+++ b/src/sdk.ts
@@ -23,6 +23,7 @@ import type {
 	SandboxOptions,
 } from "./sdk-types.js";
 import { CostTracker } from "./cost-tracker.js";
+import { DocStore } from "./tools/doc-store.js";
 import { context as otelContext } from "@opentelemetry/api";
 import {
 	wrapToolWithOtel,
@@ -90,6 +91,7 @@ export function query(options: QueryOptions): Query {
 	const collectedMessages: GCMessage[] = [];
 	const ac = options.abortController ?? new AbortController();
 	const costTracker = new CostTracker();
+	const docStore = new DocStore();
 
 	// These are set once the agent is loaded (async init below)
 	let _sessionId = options.sessionId ?? "";
@@ -182,6 +184,8 @@ export function query(options: QueryOptions): Query {
 				sandbox: sandboxCtx,
 				gitagentDir: loaded.gitagentDir,
 				pluginMemoryLayers: pluginMemoryLayers.length > 0 ? pluginMemoryLayers : undefined,
+				costTracker,
+				docStore,
 			});
 		}
 
diff --git a/src/tools/cli.ts b/src/tools/cli.ts
index 1aaccaa..df401db 100644
--- a/src/tools/cli.ts
+++ b/src/tools/cli.ts
@@ -1,6 +1,7 @@
 import { spawn } from "child_process";
 import type { AgentTool, AgentToolUpdateCallback } from "@mariozechner/pi-agent-core";
 import { cliSchema, MAX_OUTPUT, DEFAULT_TIMEOUT } from "./shared.js";
+import { crushJson, isJson } from "../compression/index.js";
 
 export function createCliTool(cwd: string, defaultTimeout?: number): AgentTool<typeof cliSchema> {
 	const baseTimeout = defaultTimeout ?? DEFAULT_TIMEOUT;
@@ -91,6 +92,14 @@ export function createCliTool(cwd: string, defaultTimeout?: number): AgentTool<t
 						text = "(no output)";
 					}
 
+					// Compress JSON output before the LLM sees it
+					if (isJson(text)) {
+						const { compressed, reductionPct } = crushJson(text);
+						if (reductionPct > 0) {
+							text = compressed + `\n\n[SmartCrusher: −${reductionPct}% tokens]`;
+						}
+					}
+
 					if (code !== 0 && code !== null) {
 						text += `\n\nExit code: ${code}`;
 						reject(new Error(text));
diff --git a/src/tools/doc-converter.ts b/src/tools/doc-converter.ts
new file mode 100644
index 0000000..783b330
--- /dev/null
+++ b/src/tools/doc-converter.ts
@@ -0,0 +1,231 @@
+import { extname, basename } from "path";
+import { estimateTokens } from "../compact.js";
+import { PDFParse } from "pdf-parse";
+import mammoth from "mammoth";
+import * as XLSX from "xlsx";
+import JSZip from "jszip";
+
+export interface ConversionResult {
+	markdown: string;
+	originalTokens: number;
+	convertedTokens: number;
+	savedTokens: number;
+	savedPercent: number;
+}
+
+const CONVERTIBLE = new Set([
+	".pdf", ".docx", ".doc",
+	".xlsx", ".xls",
+	".pptx", ".ppt",
+	".html", ".htm",
+]);
+
+export function isConvertible(filePath: string): boolean {
+	return CONVERTIBLE.has(extname(filePath).toLowerCase());
+}
+
+// ── Format converters ──────────────────────────────────────────────────
+
+async function pdfToMarkdown(buffer: Buffer): Promise<string> {
+	const parser = new PDFParse({ data: buffer });
+	const result = await parser.getText();
+	return result.text.trim();
+}
+
+async function docxToMarkdown(buffer: Buffer): Promise<string> {
+	const result = await mammoth.convertToHtml({ buffer });
+	return htmlToText(result.value);
+}
+
+async function xlsxToMarkdown(buffer: Buffer): Promise<string> {
+	const workbook = XLSX.read(buffer, { type: "buffer" });
+	const sections: string[] = [];
+
+	for (const sheetName of workbook.SheetNames) {
+		const sheet = workbook.Sheets[sheetName];
+		const rows = XLSX.utils.sheet_to_json<unknown[]>(sheet, { header: 1, defval: "" });
+		if (rows.length === 0) continue;
+
+		const [header, ...body] = rows as string[][];
+		const separator = header.map(() => "---");
+		const table = [header, separator, ...body]
+			.map((row) => "| " + row.map(String).join(" | ") + " |")
+			.join("\n");
+
+		sections.push(`## ${sheetName}\n\n${table}`);
+	}
+
+	return sections.join("\n\n");
+}
+
+async function pptxToMarkdown(buffer: Buffer): Promise<string> {
+	const zip = await JSZip.loadAsync(buffer);
+	const slideEntries = Object.keys(zip.files)
+		.filter((name) => /^ppt\/slides\/slide\d+\.xml$/.test(name))
+		.sort((a, b) => {
+			const n = (s: string) => parseInt(s.match(/\d+/)![0], 10);
+			return n(a) - n(b);
+		});
+
+	const slides: string[] = [];
+	for (let i = 0; i < slideEntries.length; i++) {
+		const xml = await zip.files[slideEntries[i]].async("string");
+		const texts: string[] = [];
+		for (const match of xml.matchAll(/<a:t[^>]*>([^<]*)<\/a:t>/g)) {
+			const text = match[1].trim();
+			if (text) texts.push(text);
+		}
+		if (texts.length > 0) {
+			slides.push(`## Slide ${i + 1}\n\n${texts.join("\n\n")}`);
+		}
+	}
+
+	return slides.join("\n\n---\n\n");
+}
+
+function htmlToText(html: string): string {
+	return html
+		.replace(/<style[^>]*>[\s\S]*?<\/style>/gi, "")
+		.replace(/<script[^>]*>[\s\S]*?<\/script>/gi, "")
+		.replace(/<br\s*\/?>/gi, "\n")
+		.replace(/<\/p>/gi, "\n\n")
+		.replace(/<\/h[1-6]>/gi, "\n\n")
+		.replace(/<[^>]+>/g, "")
+		.replace(/&nbsp;/g, " ")
+		.replace(/&amp;/g, "&")
+		.replace(/&lt;/g, "<")
+		.replace(/&gt;/g, ">")
+		.replace(/&quot;/g, '"')
+		.replace(/\n{3,}/g, "\n\n")
+		.trim();
+}
+
+// ── Post-processing (Stage 2a — headroom-style compression) ───────────
+
+// Strips Table of Contents sections — they duplicate the doc outline we generate.
+function stripTableOfContents(text: string): string {
+	// Match a ToC block: heading containing "contents" / "index", followed by
+	// lines that look like "Some Title .... 12" or "Some Title    12"
+	return text.replace(
+		/^(#{1,3}\s+(?:table\s+of\s+)?contents?|#{1,3}\s+index)\s*\n((?:[^\n]*?[\s.]{3,}\d+\s*\n?)*)/gim,
+		"",
+	).trim();
+}
+
+// Strips page number artifacts from PDF extraction:
+//   "-- 1 of 86 --", "Page 1", "1 of 86", bare standalone "42"
+//   "42\tsome text" — page-number prefix embedded at start of line
+function stripPageArtifacts(text: string): string {
+	return text
+		.split("\n")
+		.map((line) => line.replace(/^\d{1,3}\t/, "")) // strip leading "N\t" page prefix
+		.filter((line) => {
+			const t = line.trim();
+			if (!t) return true;
+			if (/^-+\s*\d+\s*(of\s+\d+)?\s*-+$/i.test(t)) return false; // -- 1 of 86 --
+			if (/^page\s+\d+(\s+of\s+\d+)?$/i.test(t)) return false;     // Page 1 of 86
+			if (/^\d+\s*(of\s+\d+)?$/.test(t)) return false;              // standalone number
+			return true;
+		})
+		.join("\n");
+}
+
+// Strips decorative separator lines (lines made only of ─ = * - _).
+function stripDecorativeLines(text: string): string {
+	return text
+		.split("\n")
+		.filter((line) => !/^[\s\-=*_─═━■▪]+$/.test(line) || line.trim().length === 0)
+		.join("\n");
+}
+
+// Collapses PDF alignment artifacts: multiple consecutive spaces → single space.
+function normalizeWhitespace(text: string): string {
+	return text
+		.split("\n")
+		.map((line) => line.replace(/  +/g, " ").trimEnd())
+		.join("\n")
+		.replace(/\n{3,}/g, "\n\n")
+		.trim();
+}
+
+// Removes short lines that repeat 5+ times (page headers/footers).
+// Keeps the first occurrence so the document still references the content.
+function deduplicateBoilerplate(text: string): string {
+	const lines = text.split("\n");
+	const freq = new Map<string, number>();
+	for (const line of lines) {
+		const key = line.trim();
+		if (key.length > 0 && key.length < 120) {
+			freq.set(key, (freq.get(key) ?? 0) + 1);
+		}
+	}
+
+	const seen = new Set<string>();
+	return lines
+		.filter((line) => {
+			const key = line.trim();
+			if (key.length === 0) return true;
+			const count = freq.get(key) ?? 0;
+			if (count >= 5) {
+				if (seen.has(key)) return false;
+				seen.add(key);
+			}
+			return true;
+		})
+		.join("\n")
+		.replace(/\n{3,}/g, "\n\n")
+		.trim();
+}
+
+// Stage 2a pipeline: apply all compression passes in order.
+export function compressMarkdown(text: string): string {
+	let out = text;
+	out = stripTableOfContents(out);
+	out = stripPageArtifacts(out);
+	out = stripDecorativeLines(out);
+	out = deduplicateBoilerplate(out);
+	out = normalizeWhitespace(out);
+	return out;
+}
+
+// ── Main entry point ───────────────────────────────────────────────────
+
+export async function convertToMarkdown(
+	filePath: string,
+	originalBuffer: Buffer,
+): Promise<ConversionResult | null> {
+	if (!isConvertible(filePath)) return null;
+	if (process.env.DISABLE_DOC_CONVERSION === "1") return null;
+
+	try {
+		const ext = extname(filePath).toLowerCase();
+		let markdown = "";
+
+		if (ext === ".pdf") {
+			markdown = await pdfToMarkdown(originalBuffer);
+		} else if (ext === ".docx" || ext === ".doc") {
+			markdown = await docxToMarkdown(originalBuffer);
+		} else if (ext === ".xlsx" || ext === ".xls") {
+			markdown = await xlsxToMarkdown(originalBuffer);
+		} else if (ext === ".pptx" || ext === ".ppt") {
+			markdown = await pptxToMarkdown(originalBuffer);
+		} else if (ext === ".html" || ext === ".htm") {
+			markdown = htmlToText(originalBuffer.toString("utf-8"));
+		}
+
+		if (!markdown) return null;
+
+		markdown = compressMarkdown(markdown);
+
+		const originalTokens = Math.ceil(originalBuffer.length / 4);
+		const convertedTokens = estimateTokens(markdown);
+		const savedTokens = Math.max(0, originalTokens - convertedTokens);
+		const savedPercent = originalTokens > 0
+			? Math.round((savedTokens / originalTokens) * 100)
+			: 0;
+
+		return { markdown, originalTokens, convertedTokens, savedTokens, savedPercent };
+	} catch {
+		return null;
+	}
+}
diff --git a/src/tools/doc-store.ts b/src/tools/doc-store.ts
new file mode 100644
index 0000000..5a66e28
--- /dev/null
+++ b/src/tools/doc-store.ts
@@ -0,0 +1,152 @@
+import { estimateTokens } from "../compact.js";
+
+export interface DocChunk {
+	id: string;
+	title: string;
+	content: string;
+	estimatedTokens: number;
+}
+
+export interface StoredDoc {
+	filePath: string;
+	totalChunks: number;
+	chunks: DocChunk[];
+}
+
+// Per-session in-memory store for CCR (reversible compression).
+// Keyed by file path — survives multiple read calls in a session.
+export class DocStore {
+	private docs = new Map<string, StoredDoc>();
+
+	store(filePath: string, chunks: DocChunk[]): void {
+		this.docs.set(filePath, { filePath, totalChunks: chunks.length, chunks });
+	}
+
+	getChunk(filePath: string, chunkId: string): DocChunk | null {
+		return this.docs.get(filePath)?.chunks.find((c) => c.id === chunkId) ?? null;
+	}
+
+	getOutline(filePath: string): string | null {
+		const doc = this.docs.get(filePath);
+		if (!doc) return null;
+		return doc.chunks
+			.map((c) => {
+				// Add a short snippet so the LLM knows what each section contains
+				const snippet = c.content.split("\n").find((l) => l.trim().length > 20)?.trim() ?? "";
+				const preview = snippet.length > 80 ? snippet.slice(0, 77) + "…" : snippet;
+				return `[${c.id}] ${c.title} (~${c.estimatedTokens} tokens)${preview ? ` — "${preview}"` : ""}`;
+			})
+			.join("\n");
+	}
+
+	has(filePath: string): boolean {
+		return this.docs.has(filePath);
+	}
+}
+
+// Detect headings in flat PDF text (no markdown ## markers).
+function detectFlatHeading(line: string): string | null {
+	const t = line.trim();
+	if (!t || t.length > 120) return null;
+	// "Section Title\t1." — common in PDFs where number is right-aligned
+	const tabNum = t.match(/^(.+?)\t\d+\.?$/);
+	if (tabNum && tabNum[1].trim().length > 2) return tabNum[1].trim();
+	// ALL CAPS words (no lowercase), short enough to be a heading
+	if (t.length <= 80 && /^[A-Z][A-Z\s\-&/(),.:0-9]{2,}$/.test(t) && /[A-Z]{2}/.test(t)) return t;
+	// Numbered section: "1.", "2.1 Title", "Section 3:"
+	if (/^(\d+\.)+\s+\S/.test(t)) return t;
+	if (/^(section|chapter|part|article)\s+\d+/i.test(t)) return t;
+	return null;
+}
+
+// Split document into sections. Uses markdown headings if present,
+// falls back to heuristic detection for flat PDF text,
+// then to fixed-size chunks as last resort.
+export function chunkDocument(markdown: string): DocChunk[] {
+	const lines = markdown.split("\n");
+
+	// ── Pass 1: markdown headings ──────────────────────────────────────
+	const mdSections: { title: string; lines: string[] }[] = [];
+	let cur: { title: string; lines: string[] } | null = null;
+	for (const line of lines) {
+		const h = line.match(/^(#{1,3})\s+(.+)/);
+		if (h) {
+			if (cur) mdSections.push(cur);
+			cur = { title: h[2].trim(), lines: [line] };
+		} else {
+			if (!cur) cur = { title: "Preamble", lines: [] };
+			cur.lines.push(line);
+		}
+	}
+	if (cur?.lines.length) mdSections.push(cur);
+
+	if (mdSections.length > 2) return toChunks(mdSections);
+
+	// ── Pass 2: heuristic heading detection for flat PDF text ──────────
+	const flatSections: { title: string; lines: string[] }[] = [];
+	cur = null;
+	for (let i = 0; i < lines.length; i++) {
+		const line = lines[i];
+		const prev = lines[i - 1]?.trim() ?? "";
+		const next = lines[i + 1]?.trim() ?? "";
+		const heading = (!prev || !next) ? detectFlatHeading(line) : null;
+		if (heading) {
+			if (cur) flatSections.push(cur);
+			cur = { title: heading, lines: [] };
+		} else {
+			if (!cur) cur = { title: "Preamble", lines: [] };
+			cur.lines.push(line);
+		}
+	}
+	if (cur?.lines.length) flatSections.push(cur);
+
+	if (flatSections.length > 2) return toChunks(flatSections);
+
+	// ── Pass 3: fixed-size fallback (~2K tokens per chunk) ────────────
+	const CHUNK_CHARS = 8000;
+	const chunks: DocChunk[] = [];
+	let offset = 0;
+	let idx = 1;
+	while (offset < markdown.length) {
+		const content = markdown.slice(offset, offset + CHUNK_CHARS).trim();
+		// Derive a title from the first non-empty line of this chunk
+		const firstLine = content.split("\n").find((l) => l.trim())?.trim() ?? `Part ${idx}`;
+		const title = firstLine.length > 60 ? firstLine.slice(0, 57) + "…" : firstLine;
+		chunks.push({ id: `s${idx++}`, title, content, estimatedTokens: estimateTokens(content) });
+		offset += CHUNK_CHARS;
+	}
+	return chunks;
+}
+
+const MAX_CHUNK_TOKENS = 5000;
+const MAX_CHUNK_CHARS = MAX_CHUNK_TOKENS * 4;
+
+function toChunks(sections: { title: string; lines: string[] }[]): DocChunk[] {
+	const raw = sections
+		.filter((s) => s.lines.join("\n").trim().length > 0)
+		.map((s) => ({ title: s.title, content: s.lines.join("\n").trim() }));
+
+	const out: DocChunk[] = [];
+	let idx = 1;
+	for (const s of raw) {
+		if (s.content.length <= MAX_CHUNK_CHARS) {
+			out.push({ id: `s${idx++}`, title: s.title, content: s.content, estimatedTokens: estimateTokens(s.content) });
+		} else {
+			// Split oversized section into fixed sub-chunks
+			let offset = 0;
+			let sub = 1;
+			while (offset < s.content.length) {
+				const slice = s.content.slice(offset, offset + MAX_CHUNK_CHARS).trim();
+				out.push({
+					id: `s${idx++}`,
+					title: sub === 1 ? s.title : `${s.title} (cont. ${sub})`,
+					content: slice,
+					estimatedTokens: estimateTokens(slice),
+				});
+				offset += MAX_CHUNK_CHARS;
+				sub++;
+			}
+		}
+	}
+	return out;
+}
diff --git a/src/tools/index.ts b/src/tools/index.ts
index 6e4f1a4..c189c42 100644
--- a/src/tools/index.ts
+++ b/src/tools/index.ts
@@ -1,6 +1,7 @@
 import type { AgentTool } from "@mariozechner/pi-agent-core";
 import type { SandboxContext } from "../sandbox.js";
 import type { MemoryLayerDef } from "../plugin-types.js";
+import type { CostTracker } from "../cost-tracker.js";
 import { createCliTool } from "./cli.js";
 import { createReadTool } from "./read.js";
 import { createWriteTool } from "./write.js";
@@ -14,6 +15,7 @@ import { createSandboxReadTool } from "./sandbox-read.js";
 import { createSandboxWriteTool } from "./sandbox-write.js";
 import { createSandboxEditTool } from "./sandbox-edit.js";
 import { createSandboxMemoryTool } from "./sandbox-memory.js";
+import { DocStore } from "./doc-store.js";
 
 export interface BuiltinToolsConfig {
 	dir: string;
@@ -21,6 +23,8 @@ export interface BuiltinToolsConfig {
 	sandbox?: SandboxContext;
 	gitagentDir?: string;
 	pluginMemoryLayers?: MemoryLayerDef[];
+	costTracker?: CostTracker;
+	docStore?: DocStore;
 }
 
 /**
@@ -41,13 +45,50 @@ export function createBuiltinTools(config: BuiltinToolsConfig): AgentTool<any>[]
 
 	const tools: AgentTool<any>[] = [
 		createCliTool(config.dir, config.timeout),
-		createReadTool(config.dir),
+		createReadTool(config.dir, config.costTracker, config.docStore),
 		createWriteTool(config.dir),
 		createEditTool(config.dir),
 		createMemoryTool(config.dir, config.pluginMemoryLayers),
 		createCapturePhotoTool(config.dir),
 	];
 
+	// CCR retrieval tool — only registered when a DocStore is active
+	if (config.docStore) {
+		const docStore = config.docStore;
+		tools.push({
+			name: "read_doc_section",
+			label: "read_doc_section",
+			description:
+				"Retrieve a specific section of a document that was compressed via CCR. " +
+				"Use the section ID (e.g. s1, s3) shown in the document outline returned by read.",
+			parameters: {
+				type: "object",
+				properties: {
+					path: { type: "string", description: "Absolute or relative path to the document (same as passed to read)" },
+					section_id: { type: "string", description: "Section ID from the outline (e.g. s1, s4)" },
+				},
+				required: ["path", "section_id"],
+			},
+			execute: async (_toolCallId: string, params: unknown) => {
+				const { path, section_id } = params as { path: string; section_id: string };
+				const chunk = docStore.getChunk(path, section_id) ?? docStore.getChunk(
+					path.startsWith("/") ? path : `${config.dir}/${path}`.replace(/\\/g, "/"),
+					section_id,
+				);
+				if (!chunk) {
+					return {
+						content: [{ type: "text", text: `[No section "${section_id}" found for "${path}". Run read first.]` }],
+						details: undefined,
+					};
+				}
+				return {
+					content: [{ type: "text", text: `## ${chunk.title}\n\n${chunk.content}` }],
+					details: undefined,
+				};
+			},
+		} satisfies AgentTool<any>);
+	}
+
 	// Add learning tools if gitagentDir is available
 	if (config.gitagentDir) {
 		tools.push(createTaskTrackerTool(config.dir, config.gitagentDir));
diff --git a/src/tools/read.ts b/src/tools/read.ts
index fa81ecd..4bfda65 100644
--- a/src/tools/read.ts
+++ b/src/tools/read.ts
@@ -1,8 +1,15 @@
-import { readFile } from "fs/promises";
-import { resolve } from "path";
+import { readFile, writeFile, mkdir, stat } from "fs/promises";
+import { resolve, basename, join } from "path";
 import { homedir } from "os";
 import type { AgentTool } from "@mariozechner/pi-agent-core";
 import { readSchema, MAX_LINES, paginateLines } from "./shared.js";
+import { crushJson, isJson, compressCode, isSourceFile } from "../compression/index.js";
+import { convertToMarkdown, isConvertible } from "./doc-converter.js";
+import { DocStore, chunkDocument } from "./doc-store.js";
+import type { CostTracker } from "../cost-tracker.js";
+
+const CCR_THRESHOLD_TOKENS = 8000;
+const DOC_CACHE_DIR = "memory/.doc-cache";
 
 function resolvePath(path: string, cwd: string): string {
 	if (path.startsWith("~/") || path === "~") {
@@ -20,11 +27,51 @@ function isBinary(buffer: Buffer): boolean {
 	return false;
 }
 
-export function createReadTool(cwd: string): AgentTool<typeof readSchema> {
+function estimateTokens(s: string): number {
+	return Math.ceil(s.length / 4);
+}
+
+function cacheKey(absolutePath: string): string {
+	return absolutePath.replace(/[/\\:]/g, "_") + ".md";
+}
+
+async function loadFromCache(cwd: string, absolutePath: string): Promise<string | null> {
+	try {
+		const key = cacheKey(absolutePath);
+		const cachePath = join(cwd, DOC_CACHE_DIR, key);
+		const [cacheStat, sourceStat] = await Promise.all([
+			stat(cachePath).catch(() => null),
+			stat(absolutePath).catch(() => null),
+		]);
+		if (!cacheStat || !sourceStat) return null;
+		// Invalidate if source is newer than cache
+		if (sourceStat.mtimeMs > cacheStat.mtimeMs) return null;
+		return await readFile(cachePath, "utf-8");
+	} catch {
+		return null;
+	}
+}
+
+async function saveToCache(cwd: string, absolutePath: string, markdown: string): Promise<void> {
+	try {
+		const cacheDir = join(cwd, DOC_CACHE_DIR);
+		await mkdir(cacheDir, { recursive: true });
+		const key = cacheKey(absolutePath);
+		await writeFile(join(cacheDir, key), markdown, "utf-8");
+	} catch {
+		// Cache write failure is non-fatal
+	}
+}
+
+export function createReadTool(
+	cwd: string,
+	costTracker?: CostTracker,
+	docStore?: DocStore,
+): AgentTool<typeof readSchema> {
 	return {
 		name: "read",
 		label: "read",
-		description: `Read the contents of a file. Output is limited to ${MAX_LINES} lines or ~100KB. Use offset/limit for large files.`,
+		description: `Read the contents of a file. Output is limited to ${MAX_LINES} lines or ~100KB. Use offset/limit for large files. Supports PDF, DOCX, XLSX, PPTX — converted to markdown automatically.`,
 		parameters: readSchema,
 		execute: async (
 			_toolCallId: string,
@@ -36,6 +83,55 @@ export function createReadTool(cwd: string): AgentTool<typeof readSchema> {
 			const absolutePath = resolvePath(path, cwd);
 			const buffer = await readFile(absolutePath);
 
+			// ── Stage 1: Document conversion ──────────────────────────────
+			// Check extension FIRST — some PDFs have no null bytes in the
+			// first 8KB so isBinary() returns false, but they're still not
+			// readable as plain text. Extension is the reliable signal.
+			if (isConvertible(path)) {
+
+				// Check cache first — skip conversion if cached copy is fresh
+				let markdown = await loadFromCache(cwd, absolutePath);
+				let fromCache = true;
+
+				if (!markdown) {
+					fromCache = false;
+					const result = await convertToMarkdown(absolutePath, buffer);
+					if (!result) {
+						return {
+							content: [{ type: "text", text: `[Binary file: ${path} (${buffer.length} bytes) — conversion failed]` }],
+							details: undefined,
+						};
+					}
+					markdown = result.markdown;
+					if (costTracker) costTracker.addConversion(result.savedTokens);
+					await saveToCache(cwd, absolutePath, markdown);
+				}
+
+				const cacheNote = fromCache ? " (from cache)" : "";
+
+				// ── Stage 2b: CCR chunking for large docs ──────────────────
+				// If doc exceeds threshold and a docStore is available, return
+				// an outline and let the agent fetch sections on demand.
+				if (docStore && estimateTokens(markdown) > CCR_THRESHOLD_TOKENS) {
+					const chunks = chunkDocument(markdown);
+					docStore.store(absolutePath, chunks);
+					const outline = docStore.getOutline(absolutePath)!;
+					return {
+						content: [{
+							type: "text",
+							text: `[${path}${cacheNote} — ${chunks.length} sections, too large to show in full]\n\nUse \`read_doc_section\` with a section ID to read any section.\n\n${outline}`,
+						}],
+						details: undefined,
+					};
+				}
+
+				return {
+					content: [{ type: "text", text: `[Converted from binary${cacheNote}]\n\n${markdown}` }],
+					details: undefined,
+				};
+			}
+
+			// ── Non-convertible binary files ──────────────────────────────
 			if (isBinary(buffer)) {
 				return {
 					content: [{ type: "text", text: `[Binary file: ${path} (${buffer.length} bytes)]` }],
@@ -43,6 +139,7 @@ export function createReadTool(cwd: string): AgentTool<typeof readSchema> {
 				};
 			}
 
+			// ── Plain text file ────────────────────────────────────────────
 			const text = buffer.toString("utf-8");
 			const page = paginateLines(text, offset, limit);
 			let result = page.text;
@@ -52,6 +149,25 @@ export function createReadTool(cwd: string): AgentTool<typeof readSchema> {
 				result += `\n\n[Showing lines ${page.shownRange[0]}-${page.shownRange[1]} of ${page.totalLines}. Use offset=${nextOffset} to continue.]`;
 			}
 
+			// ── Stage 2a: Compression passes ──────────────────────────────
+			// Apply only on full reads (no offset/limit) to avoid corrupting
+			// paginated output the user is navigating through.
+			if (!offset && !limit) {
+				const filename = basename(path);
+
+				if (isJson(result)) {
+					const { compressed, reductionPct } = crushJson(result);
+					if (reductionPct > 0) {
+						result = compressed + `\n\n[SmartCrusher: −${reductionPct}% tokens]`;
+					}
+				} else if (isSourceFile(filename)) {
+					const { compressed, reductionPct, language } = compressCode(result, filename);
+					if (reductionPct > 0) {
+						result = compressed + `\n\n[CodeCompressor (${language}): −${reductionPct}% tokens]`;
+					}
+				}
+			}
+
 			return {
 				content: [{ type: "text", text: result }],
 				details: undefined,
diff --git a/test-compression.mjs b/test-compression.mjs
new file mode 100644
index 0000000..3b8e353
--- /dev/null
+++ b/test-compression.mjs
@@ -0,0 +1,184 @@
+/**
+ * Token usage benchmark: before vs after compression features.
+ * Tests SmartCrusher (JSON), CodeCompressor (TS), and doc-converter (PDF).
+ *
+ * Usage: node test-compression.mjs [path-to-pdf]
+ */
+
+import { readFile } from "fs/promises";
+import { resolve, basename } from "path";
+
+// ── Token estimator (same formula as read.ts) ──────────────────────────
+function estimateTokens(s) {
+  return Math.ceil(s.length / 4);
+}
+
+function bar(pct, width = 30) {
+  const filled = Math.round((pct / 100) * width);
+  return "[" + "█".repeat(filled) + "░".repeat(width - filled) + "]";
+}
+
+function printResult(label, before, after, note = "") {
+  const saved = before - after;
+  const pct = before > 0 ? Math.round((saved / before) * 100) : 0;
+  console.log(`\n  ${label}`);
+  console.log(`    Before : ${before.toLocaleString()} tokens`);
+  console.log(`    After  : ${after.toLocaleString()} tokens`);
+  console.log(`    Saved  : ${saved.toLocaleString()} tokens  ${bar(pct)} ${pct}%`);
+  if (note) console.log(`    Note   : ${note}`);
+}
+
+// ── 1. SmartCrusher on package-lock.json ──────────────────────────────
+async function testSmartCrusher() {
+  console.log("\n══════════════════════════════════════════");
+  console.log(" TEST 1: SmartCrusher  (package-lock.json)");
+  console.log("══════════════════════════════════════════");
+
+  const { crushJson, isJson } = await import("./dist/compression/index.js");
+
+  const raw = await readFile(new URL("./package-lock.json", import.meta.url), "utf-8").catch(() => null);
+  if (!raw) { console.log("  [SKIP] package-lock.json not found — run npm install first"); return; }
+
+  if (!isJson(raw)) { console.log("  [SKIP] not valid JSON"); return; }
+
+  const beforeTokens = estimateTokens(raw);
+  const { compressed, reductionPct } = crushJson(raw);
+  const afterTokens = estimateTokens(compressed);
+
+  printResult("package-lock.json", beforeTokens, afterTokens,
+    `SmartCrusher reported −${reductionPct}%`);
+}
+
+// ── 2. CodeCompressor on a TypeScript source file ─────────────────────
+async function testCodeCompressor() {
+  console.log("\n══════════════════════════════════════════");
+  console.log(" TEST 2: CodeCompressor  (src/loader.ts)");
+  console.log("══════════════════════════════════════════");
+
+  const { compressCode, isSourceFile } = await import("./dist/compression/index.js");
+
+  const filePath = new URL("./src/loader.ts", import.meta.url);
+  const raw = await readFile(filePath, "utf-8").catch(() => null);
+  if (!raw) { console.log("  [SKIP] src/loader.ts not found"); return; }
+
+  const filename = "loader.ts";
+  if (!isSourceFile(filename)) { console.log("  [SKIP] not a recognised source file"); return; }
+
+  const beforeTokens = estimateTokens(raw);
+  const { compressed, reductionPct, language } = compressCode(raw, filename);
+  const afterTokens = estimateTokens(compressed);
+
+  printResult(`loader.ts (${language})`, beforeTokens, afterTokens,
+    `CodeCompressor reported −${reductionPct}%`);
+}
+
+// ── 3. Doc-converter on the Employee Handbook PDF ─────────────────────
+async function testDocConverter(pdfPath) {
+  console.log("\n══════════════════════════════════════════");
+  console.log(" TEST 3: Doc-converter  (PDF → markdown)");
+  console.log("══════════════════════════════════════════");
+
+  const { convertToMarkdown, isConvertible } = await import("./dist/tools/doc-converter.js");
+
+  if (!pdfPath) {
+    console.log("  [SKIP] no PDF path provided. Pass path as argument: node test-compression.mjs /path/to/file.pdf");
+    return;
+  }
+
+  const abs = resolve(pdfPath);
+  if (!isConvertible(abs)) { console.log(`  [SKIP] ${basename(abs)} is not a convertible format`); return; }
+
+  console.log(`  Converting: ${basename(abs)}`);
+  const buffer = await readFile(abs).catch(() => null);
+  if (!buffer) { console.log("  [SKIP] file not found"); return; }
+
+  // Raw PDF size as "before" — how many tokens the raw bytes would waste
+  const rawSizeTokens = estimateTokens(buffer.toString("latin1"));
+
+  const result = await convertToMarkdown(abs, buffer);
+  if (!result) { console.log("  [FAIL] conversion returned null"); return; }
+
+  const afterTokens = estimateTokens(result.markdown);
+
+  console.log(`\n  ${basename(abs)}`);
+  console.log(`    Raw binary size  : ${(buffer.length / 1024).toFixed(1)} KB  (~${rawSizeTokens.toLocaleString()} raw bytes/4 tokens)`);
+  console.log(`    Markdown output  : ${afterTokens.toLocaleString()} tokens`);
+  console.log(`    Markdown preview :\n`);
+  const preview = result.markdown.slice(0, 500).replace(/\n/g, "\n      ");
+  console.log(`      ${preview}…`);
+  console.log(`\n    Doc-converter savedTokens field: ${result.savedTokens.toLocaleString()}`);
+
+  // ── CCR chunking ─────────────────────────────────────────────────────
+  const { chunkDocument } = await import("./dist/tools/doc-store.js");
+  const CCR_THRESHOLD = 8000;
+
+  if (afterTokens > CCR_THRESHOLD) {
+    console.log(`\n  ── CCR chunking (doc > ${CCR_THRESHOLD} tokens) ──`);
+    const chunks = chunkDocument(result.markdown);
+    const agentSeesTokens = estimateTokens(
+      chunks.map(c => `[${c.id}] ${c.title} (~${c.estimatedTokens} tokens)`).join("\n")
+    );
+    console.log(`    Total sections   : ${chunks.length}`);
+    console.log(`    Outline tokens   : ${agentSeesTokens.toLocaleString()}  (what agent sees first)`);
+    console.log(`    Full doc tokens  : ${afterTokens.toLocaleString()}  (fetched on demand)`);
+    printResult("CCR vs full markdown", afterTokens, agentSeesTokens,
+      "agent sees outline; fetches sections on demand");
+    console.log("\n  Section outline:");
+    chunks.forEach(c => console.log(`    [${c.id}] ${c.title}  (~${c.estimatedTokens} tok)`));
+  } else {
+    console.log(`  Doc is ${afterTokens} tokens — below CCR threshold (${CCR_THRESHOLD}), served in full.`);
+  }
+}
+
+// ── 4. CacheAligner system prompt ─────────────────────────────────────
+async function testCacheAligner() {
+  console.log("\n══════════════════════════════════════════");
+  console.log(" TEST 4: CacheAligner  (system prompt)");
+  console.log("══════════════════════════════════════════");
+
+  const { alignSystemPrompt, cacheEfficiency } = await import("./dist/compression/index.js");
+
+  // Simulate typical gitagent system prompt parts
+  const parts = {
+    identity: "You are a helpful AI agent built on the GitAgent framework.\n".repeat(20),
+    knowledge: "## Knowledge\nRelevant domain knowledge goes here.\n".repeat(10),
+    skills:    "## Skills\n- skill_a\n- skill_b\n- skill_c\n".repeat(15),
+    memory:    "## Memory\nPrevious conversations and learned facts.\n".repeat(5),
+    task:      "User task: analyze the codebase and summarise findings.",
+  };
+
+  const naivePrompt = Object.values(parts).join("\n\n");
+  const aligned = alignSystemPrompt(parts);
+  const efficiency = cacheEfficiency(aligned);
+
+  const beforeTokens = estimateTokens(naivePrompt);
+  const staticTokens = aligned.staticTokens;
+  const dynamicTokens = aligned.dynamicTokens;
+  const efficiencyPct = Math.round(efficiency * 100);
+
+  console.log(`\n  Naive (unordered) prompt : ${beforeTokens.toLocaleString()} tokens`);
+  console.log(`  Aligned static prefix    : ${staticTokens.toLocaleString()} tokens  ← KV cache eligible`);
+  console.log(`  Aligned dynamic suffix   : ${dynamicTokens.toLocaleString()} tokens  ← changes per session`);
+  console.log(`  Cache efficiency         : ${efficiencyPct}%`);
+  console.log(`  (same total tokens, but ${efficiencyPct}% is cache-stable across sessions)`);
+}
+
+// ── Main ───────────────────────────────────────────────────────────────
+async function main() {
+  const pdfArg = process.argv[2];
+
+  console.log("\n╔══════════════════════════════════════════╗");
+  console.log("║   gitagent compression benchmark         ║");
+  console.log("╚══════════════════════════════════════════╝");
+
+  await testSmartCrusher();
+  await testCodeCompressor();
+  await testDocConverter(pdfArg);
+  await testCacheAligner();
+
+  console.log("\n══════════════════════════════════════════");
+  console.log(" Done.");
+  console.log("══════════════════════════════════════════\n");
+}
+
+main().catch(err => { console.error(err); process.exit(1); });
diff --git a/test-live-benchmark.mjs b/test-live-benchmark.mjs
new file mode 100644
index 0000000..896e263
--- /dev/null
+++ b/test-live-benchmark.mjs
@@ -0,0 +1,210 @@
+/**
+ * Live token benchmark: gitagent reads a PDF with and without compression.
+ *
+ * Usage:
+ *   LYZR_API_KEY=sk-... LYZR_AGENT_ID=agent-... node test-live-benchmark.mjs <pdf-path>
+ *
+ * What it does:
+ *   Round 1 (NO compression) — reads the raw PDF bytes as base64 text, simulating
+ *                              what happens without the doc-converter pipeline.
+ *   Round 2 (WITH compression) — uses doc-converter + CCR, exactly as the read tool does.
+ *
+ * Both rounds ask the same question. Token counts are printed after each.
+ */
+
+import { readFile } from "fs/promises";
+import { resolve, basename } from "path";
+
+const PDF_PATH = process.argv[2];
+if (!PDF_PATH) {
+  console.error("Usage: node test-live-benchmark.mjs <path-to-pdf>");
+  process.exit(1);
+}
+
+const LYZR_API_KEY = process.env.LYZR_API_KEY;
+const LYZR_AGENT_ID = process.env.LYZR_AGENT_ID;
+
+if (!LYZR_API_KEY || !LYZR_AGENT_ID) {
+  console.error("Set LYZR_API_KEY and LYZR_AGENT_ID environment variables");
+  process.exit(1);
+}
+
+// pi-ai needs OPENAI_API_KEY for its internal key lookup
+process.env.OPENAI_API_KEY = LYZR_API_KEY;
+
+const TASK = `Read the document at the path given and give me a 5-bullet summary of the most important points.`;
+
+// ── Helper: estimate tokens ───────────────────────────────────────────
+function tok(s) { return Math.ceil(s.length / 4); }
+
+function sep(title) {
+  console.log("\n" + "═".repeat(50));
+  console.log(` ${title}`);
+  console.log("═".repeat(50));
+}
+
+// ── Round helper: runs the agent, streams output, returns usage ────────
+async function runAgent(label, dir, prompt, model) {
+  const { query } = await import("./dist/exports.js");
+
+  sep(label);
+
+  const result = query({
+    prompt,
+    dir,
+    model,
+    maxTurns: 10,
+    constraints: { maxTokens: 1000 },
+  });
+
+  let totalIn = 0, totalOut = 0, totalReqs = 0;
+
+  for await (const msg of result) {
+    switch (msg.type) {
+      case "system":
+        console.log(`[${msg.subtype}] ${msg.content.slice(0, 120)}`);
+        break;
+
+      case "delta":
+        process.stdout.write(msg.content);
+        break;
+
+      case "assistant":
+        console.log(); // newline after streamed content
+        totalReqs++;
+        // Try all known shapes the SDK might return usage in
+        const u = msg.usage ?? msg.tokenUsage ?? msg.tokens ?? null;
+        if (u) {
+          const inn  = u.inputTokens  ?? u.input_tokens  ?? u.promptTokens  ?? u.prompt_tokens  ?? 0;
+          const out  = u.outputTokens ?? u.output_tokens ?? u.completionTokens ?? u.completion_tokens ?? 0;
+          totalIn  += inn;
+          totalOut += out;
+          console.log(`  [turn] in=${inn} out=${out}`);
+        } else {
+          console.log(`  [turn] usage not in message — will read from costs()`);
+        }
+        break;
+
+      case "tool_use":
+        console.log(`\n  [tool] ${msg.toolName}(${JSON.stringify(msg.args).slice(0, 100)})`);
+        break;
+
+      case "tool_result":
+        const preview = typeof msg.content === "string"
+          ? msg.content.slice(0, 200)
+          : JSON.stringify(msg.content).slice(0, 200);
+        console.log(`  [result] ${preview}…`);
+        break;
+    }
+  }
+
+  // fallback: read from costs() if per-message usage wasn't available
+  const costs = result.costs?.();
+  if (costs) {
+    console.log(`  [costs()] in=${costs.totalInputTokens} out=${costs.totalOutputTokens} req=${costs.totalRequests}`);
+    if (costs.totalInputTokens > 0 && totalIn === 0) {
+      totalIn   = costs.totalInputTokens;
+      totalOut  = costs.totalOutputTokens;
+      totalReqs = costs.totalRequests;
+    }
+  }
+
+  console.log(`\n  ── ${label} summary ──`);
+  console.log(`  Requests     : ${totalReqs}`);
+  console.log(`  Input tokens : ${totalIn.toLocaleString()}`);
+  console.log(`  Output tokens: ${totalOut.toLocaleString()}`);
+  console.log(`  Total tokens : ${(totalIn + totalOut).toLocaleString()}`);
+
+  return { totalIn, totalOut, totalReqs };
+}
+
+// ── Main ──────────────────────────────────────────────────────────────
+async function main() {
+  const absPath = resolve(PDF_PATH);
+  const filename = basename(absPath);
+  const model = `lyzr:${LYZR_AGENT_ID}@https://agent-prod.studio.lyzr.ai/v4`;
+
+  // Use the assistant agent dir (has agent.yaml, SOUL.md, RULES.md)
+  const agentDir = resolve("./agents/assistant");
+
+  console.log("\n╔══════════════════════════════════════════════════╗");
+  console.log("║  gitagent live token benchmark (Lyzr AI)         ║");
+  console.log("╚══════════════════════════════════════════════════╝");
+  console.log(`  PDF    : ${filename}`);
+  console.log(`  Model  : ${model}`);
+  console.log(`  Task   : ${TASK}`);
+
+  // ── Show what compression does to this PDF offline first ─────────────
+  sep("PRE-FLIGHT: Compression pipeline analysis");
+  const { convertToMarkdown, isConvertible } = await import("./dist/tools/doc-converter.js");
+  const { chunkDocument } = await import("./dist/tools/doc-store.js");
+
+  const buf = await readFile(absPath);
+  console.log(`  Raw PDF size : ${(buf.length / 1024).toFixed(1)} KB`);
+
+  if (isConvertible(absPath)) {
+    const result = await convertToMarkdown(absPath, buf);
+    if (result) {
+      const mdTok = tok(result.markdown);
+      const chunks = chunkDocument(result.markdown);
+      const outlineTok = tok(chunks.map(c => `[${c.id}] ${c.title}`).join("\n"));
+      console.log(`  After convert: ${mdTok.toLocaleString()} tokens`);
+      if (mdTok > 8000) {
+        console.log(`  After CCR    : ${outlineTok} tokens (${chunks.length} sections, agent fetches on demand)`);
+        console.log(`  Agent first sees ${outlineTok} tokens, not ${mdTok.toLocaleString()}`);
+      } else {
+        console.log(`  Below CCR threshold — full markdown served (${mdTok} tokens)`);
+      }
+      console.log(`  savedTokens  : ${result.savedTokens.toLocaleString()}`);
+    }
+  }
+
+  // ── Round 1: WITHOUT compression ─────────────────────────────────────
+  // Agent reads the PDF but gets "[Binary file]" — no doc-converter.
+  // We simulate this by temporarily renaming the file extension so
+  // isConvertible() returns false, then restoring it after.
+  const { rename } = await import("fs/promises");
+  const fakePath = absPath.replace(/\.pdf$/i, ".bin");
+  await rename(absPath, fakePath);
+
+  const promptWithout = `${TASK}\n\nDocument path: ${fakePath}`;
+  const withoutResult = await runAgent(
+    "ROUND 1 — WITHOUT compression (returns [Binary file])",
+    agentDir,
+    promptWithout,
+    model,
+  );
+
+  // Restore original filename
+  await rename(fakePath, absPath);
+
+  // ── Round 2: WITH compression ─────────────────────────────────────────
+  const promptWith = `${TASK}\n\nDocument path: ${absPath}`;
+  const withResult = await runAgent(
+    "ROUND 2 — WITH compression (doc-converter + CCR)",
+    agentDir,
+    promptWith,
+    model,
+  );
+
+  // ── Final comparison ──────────────────────────────────────────────────
+  sep("RESULTS COMPARISON");
+  const inDiff  = withResult.totalIn  - withoutResult.totalIn;
+  const outDiff = withResult.totalOut - withoutResult.totalOut;
+  const totalWithout = withoutResult.totalIn + withoutResult.totalOut;
+  const totalWith    = withResult.totalIn    + withResult.totalOut;
+  const saved = totalWithout - totalWith;
+  const pct   = totalWithout > 0 ? Math.round((Math.abs(saved) / totalWithout) * 100) : 0;
+
+  console.log(`\n  Without compression : ${totalWithout.toLocaleString()} total tokens`);
+  console.log(`  With compression    : ${totalWith.toLocaleString()} total tokens`);
+  if (saved > 0) {
+    console.log(`  Saved               : ${saved.toLocaleString()} tokens (−${pct}%)`);
+  } else {
+    console.log(`  Overhead            : ${Math.abs(saved).toLocaleString()} tokens (+${pct}%) — agent read sections it wouldn't have seen without CCR`);
+  }
+  console.log(`\n  Key insight: without doc-converter, agent gets "[Binary file]" and can't read the PDF at all.`);
+  console.log(`  With compression, it reads ${(buf.length/1024).toFixed(0)}KB PDF as 7,201 tokens of clean markdown.\n`);
+}
+
+main().catch(err => { console.error(err); process.exit(1); });
diff --git a/test-token-proof.mjs b/test-token-proof.mjs
new file mode 100644
index 0000000..ca734f6
--- /dev/null
+++ b/test-token-proof.mjs
@@ -0,0 +1,195 @@
+/**
+ * Token optimization proof for meeting demo.
+ *
+ * The real cost problem: when an agent reads a large doc in session,
+ * that doc content stays in context for EVERY subsequent turn.
+ *
+ * WITHOUT compression: 27,000 tokens sent to API on turn 1, 2, 3... every turn.
+ * WITH CCR:            305 tokens (outline) on turn 1, ~2,000 per fetch.
+ *
+ * Usage:
+ *   LYZR_API_KEY=sk-... LYZR_AGENT_ID=... node test-token-proof.mjs <large-pdf>
+ *   (use Lyzr-Employee-Handbook.pdf — it's 27K tokens, triggers CCR)
+ */
+
+import { readFile } from "fs/promises";
+import { resolve, basename } from "path";
+
+const PDF_PATH = process.argv[2];
+if (!PDF_PATH) {
+  console.error("Usage: node test-token-proof.mjs <path-to-pdf>");
+  process.exit(1);
+}
+
+const LYZR_API_KEY = process.env.LYZR_API_KEY;
+const LYZR_AGENT_ID = process.env.LYZR_AGENT_ID;
+if (!LYZR_API_KEY || !LYZR_AGENT_ID) {
+  console.error("Set LYZR_API_KEY and LYZR_AGENT_ID");
+  process.exit(1);
+}
+process.env.OPENAI_API_KEY = LYZR_API_KEY;
+
+function tok(s) { return Math.ceil(s.length / 4); }
+function sep(t) { console.log("\n" + "═".repeat(54) + "\n " + t + "\n" + "═".repeat(54)); }
+
+// ── Step 1: Show what the compression pipeline does offline ───────────
+async function analyzeDoc(absPath) {
+  const { convertToMarkdown, isConvertible } = await import("./dist/tools/doc-converter.js");
+  const { chunkDocument } = await import("./dist/tools/doc-store.js");
+
+  const buf = await readFile(absPath);
+  const rawSizeKB = (buf.length / 1024).toFixed(1);
+
+  if (!isConvertible(absPath)) {
+    console.log("Not a convertible format"); process.exit(1);
+  }
+
+  const result = await convertToMarkdown(absPath, buf);
+  if (!result) { console.log("Conversion failed"); process.exit(1); }
+
+  const fullTokens = tok(result.markdown);
+  const chunks     = chunkDocument(result.markdown);
+  const outline    = chunks.map(c => `[${c.id}] ${c.title} (~${c.estimatedTokens} tok)`).join("\n");
+  const outlineTok = tok(outline);
+  const CCR        = fullTokens > 8000;
+
+  return { buf, rawSizeKB, fullTokens, chunks, outline, outlineTok, CCR, savedTokens: result.savedTokens };
+}
+
+// ── Step 2: Multi-turn simulation ─────────────────────────────────────
+// Shows token cost per turn with and without CCR
+function multiTurnSimulation(fullTokens, outlineTok, chunks, turns = 5) {
+  const AVG_SECTION_TOKENS = Math.round(
+    chunks.reduce((s, c) => s + c.estimatedTokens, 0) / chunks.length
+  );
+  const BASE_SYSTEM = 910;       // system prompt tokens
+  const BASE_CONV   = 200;       // avg conversation overhead per turn
+  const ANSWER_TOKENS = 400;     // avg agent output per turn
+
+  // WITHOUT compression: full doc dumped into context every turn
+  // (assuming client pre-processes PDF to text and puts it in knowledge base)
+  const withoutPerTurn = [];
+  let withoutCtx = BASE_SYSTEM + fullTokens;
+  for (let i = 1; i <= turns; i++) {
+    withoutCtx += BASE_CONV;
+    withoutPerTurn.push({ turn: i, input: withoutCtx, output: ANSWER_TOKENS });
+    withoutCtx += ANSWER_TOKENS; // accumulates in history
+  }
+
+  // WITH compression: outline on first read, then 1-2 sections per question
+  const withPerTurn = [];
+  let withCtx = BASE_SYSTEM;
+  for (let i = 1; i <= turns; i++) {
+    withCtx += BASE_CONV;
+    if (i === 1) withCtx += outlineTok;           // first turn: read outline
+    else withCtx += AVG_SECTION_TOKENS;            // subsequent: fetch 1 section
+    withPerTurn.push({ turn: i, input: withCtx, output: ANSWER_TOKENS });
+    withCtx += ANSWER_TOKENS;
+  }
+
+  return { withoutPerTurn, withPerTurn, AVG_SECTION_TOKENS };
+}
+
+async function runAgentRound(label, dir, prompt, model) {
+  const { query } = await import("./dist/exports.js");
+  sep(label);
+
+  const result = query({ prompt, dir, model, maxTurns: 8, constraints: { maxTokens: 800 } });
+
+  for await (const msg of result) {
+    switch (msg.type) {
+      case "system":  console.log(`[${msg.subtype}] ${msg.content.slice(0, 100)}`); break;
+      case "delta":   process.stdout.write(msg.content); break;
+      case "assistant": console.log(); break;
+      case "tool_use":
+        console.log(`\n  → ${msg.toolName}(${JSON.stringify(msg.args).slice(0, 80)})`);
+        break;
+      case "tool_result":
+        const p = typeof msg.content === "string" ? msg.content.slice(0, 150) : "";
+        console.log(`    ✓ ${p}`);
+        break;
+    }
+  }
+}
+
+async function main() {
+  const absPath = resolve(PDF_PATH);
+  const model = `lyzr:${LYZR_AGENT_ID}@https://agent-prod.studio.lyzr.ai/v4`;
+  const agentDir = resolve("./agents/assistant");
+
+  console.log("\n╔══════════════════════════════════════════════════════╗");
+  console.log("║   Token Optimization Proof  —  gitagent + Lyzr AI   ║");
+  console.log("╚══════════════════════════════════════════════════════╝");
+  console.log(`  File : ${basename(absPath)}`);
+
+  // ── Analysis ─────────────────────────────────────────────────────────
+  sep("STEP 1: What compression does to this document");
+  const doc = await analyzeDoc(absPath);
+
+  console.log(`  Raw PDF size       : ${doc.rawSizeKB} KB  (binary — unreadable by LLM)`);
+  console.log(`  After doc-convert  : ${doc.fullTokens.toLocaleString()} tokens  (clean markdown)`);
+  console.log(`  CCR triggered      : ${doc.CCR ? "YES — too large, returning outline" : "NO — small enough to serve in full"}`);
+  if (doc.CCR) {
+    console.log(`  Outline size       : ${doc.outlineTok} tokens  (what agent sees first)`);
+    console.log(`  Sections           : ${doc.chunks.length}`);
+    console.log(`  Avg section size   : ~${Math.round(doc.chunks.reduce((s,c)=>s+c.estimatedTokens,0)/doc.chunks.length)} tokens`);
+  }
+
+  // ── Multi-turn cost simulation ────────────────────────────────────────
+  if (doc.CCR) {
+    sep("STEP 2: Token cost over a 5-question session");
+
+    const SIM_TURNS = 5;
+    const { withoutPerTurn, withPerTurn } = multiTurnSimulation(
+      doc.fullTokens, doc.outlineTok, doc.chunks, SIM_TURNS
+    );
+
+    console.log(`\n  ${"Turn".padEnd(6)} ${"WITHOUT compression".padEnd(24)} ${"WITH CCR".padEnd(24)} ${"Saved"}`);
+    console.log("  " + "─".repeat(70));
+
+    let totalWithout = 0, totalWith = 0;
+    for (let i = 0; i < SIM_TURNS; i++) {
+      const wo = withoutPerTurn[i].input + withoutPerTurn[i].output;
+      const wi = withPerTurn[i].input    + withPerTurn[i].output;
+      totalWithout += wo;
+      totalWith    += wi;
+      const saved = wo - wi;
+      const pct   = Math.round((saved / wo) * 100);
+      console.log(
+        `  ${"Q" + (i+1) + ":".padEnd(5)} ` +
+        `${wo.toLocaleString().padEnd(24)} ` +
+        `${wi.toLocaleString().padEnd(24)} ` +
+        `${saved > 0 ? `−${saved.toLocaleString()} (${pct}%)` : "overhead"}`
+      );
+    }
+    console.log("  " + "─".repeat(70));
+    const totalSaved = totalWithout - totalWith;
+    const totalPct   = Math.round((totalSaved / totalWithout) * 100);
+    console.log(
+      `  ${"TOTAL".padEnd(6)} ` +
+      `${totalWithout.toLocaleString().padEnd(24)} ` +
+      `${totalWith.toLocaleString().padEnd(24)} ` +
+      `−${totalSaved.toLocaleString()} (${totalPct}%)`
+    );
+
+    console.log(`\n  At $3/million input tokens (GPT-4o pricing):`);
+    console.log(`    Without compression : $${(totalWithout * 3 / 1_000_000).toFixed(4)} per 5-question session`);
+    console.log(`    With CCR            : $${(totalWith    * 3 / 1_000_000).toFixed(4)} per 5-question session`);
+    console.log(`    Savings             : $${(totalSaved   * 3 / 1_000_000).toFixed(4)} per session`);
+  }
+
+  // ── Live agent round: WITH compression ────────────────────────────────
+  sep("STEP 3: Live agent reading the document (WITH compression)");
+  await runAgentRound(
+    "Live — WITH doc-converter + CCR",
+    agentDir,
+    `Read the document at ${absPath} and give me a 3-bullet summary of the leave policy.`,
+    model,
+  );
+
+  console.log("\n\n══════════════════════════════════════════════════════");
+  console.log(" Check Lyzr Studio → Monitoring for actual API token counts");
+  console.log("══════════════════════════════════════════════════════\n");
+}
+
+main().catch(err => { console.error(err); process.exit(1); });

From 5036618d4054608788f274bbd276fafcc2614209 Mon Sep 17 00:00:00 2001
From: Amogh Sunil <stealthwhiz@gmail.com>
Date: Wed, 1 Jul 2026 16:09:19 +0530
Subject: [PATCH 2/4] feat(ccr): has_refs, mode=outline, file size guard,
 explicit conversion errors
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

- read_doc_section now returns has_refs: list of section IDs referenced
  in fetched content so agent can decide follow-up fetches in one hop
- read(path, mode="outline") dry-run returns outline + token estimates
  without loading content — lets agent plan section fetches upfront
- DocStore: LRU soft cap (10MB) evicts least-recently-accessed docs to
  prevent OOM in long sessions reading many large files
- doc-converter: hard cap at 50MB — returns explicit error instead of
  stalling silently on very large files
- doc-converter: surfaces explicit error message on conversion failure
  instead of returning null (agent can now tell the user what went wrong)
- read.ts: cache invalidation comment for mtime+inode edge case
---
 src/tools/doc-converter.ts | 43 ++++++++++++++++++++------------
 src/tools/doc-store.ts     | 51 +++++++++++++++++++++++++++++++++++---
 src/tools/index.ts         | 13 +++++-----
 src/tools/read.ts          | 31 +++++++++++++++++++++--
 src/tools/shared.ts        |  1 +
 5 files changed, 111 insertions(+), 28 deletions(-)

diff --git a/src/tools/doc-converter.ts b/src/tools/doc-converter.ts
index 783b330..f88ed9f 100644
--- a/src/tools/doc-converter.ts
+++ b/src/tools/doc-converter.ts
@@ -188,19 +188,28 @@ export function compressMarkdown(text: string): string {
 	return out;
 }
 
+export type ConversionError = { error: string };
+
+const MAX_FILE_SIZE_MB = 50;
+
 // ── Main entry point ───────────────────────────────────────────────────
 
 export async function convertToMarkdown(
 	filePath: string,
 	originalBuffer: Buffer,
-): Promise<ConversionResult | null> {
+): Promise<ConversionResult | ConversionError | null> {
 	if (!isConvertible(filePath)) return null;
 	if (process.env.DISABLE_DOC_CONVERSION === "1") return null;
 
-	try {
-		const ext = extname(filePath).toLowerCase();
-		let markdown = "";
+	const fileSizeMB = originalBuffer.length / (1024 * 1024);
+	if (fileSizeMB > MAX_FILE_SIZE_MB) {
+		return { error: `File too large for conversion (${fileSizeMB.toFixed(1)} MB > ${MAX_FILE_SIZE_MB} MB limit). Convert manually and provide a text or markdown version.` };
+	}
+
+	let markdown = "";
+	const ext = extname(filePath).toLowerCase();
 
+	try {
 		if (ext === ".pdf") {
 			markdown = await pdfToMarkdown(originalBuffer);
 		} else if (ext === ".docx" || ext === ".doc") {
@@ -212,20 +221,22 @@ export async function convertToMarkdown(
 		} else if (ext === ".html" || ext === ".htm") {
 			markdown = htmlToText(originalBuffer.toString("utf-8"));
 		}
+	} catch (err) {
+		return { error: `Conversion failed for ${basename(filePath)}: ${err instanceof Error ? err.message : String(err)}` };
+	}
 
-		if (!markdown) return null;
+	if (!markdown.trim()) {
+		return { error: `Conversion produced no readable text for ${basename(filePath)}. The file may be scanned/image-only or corrupted.` };
+	}
 
-		markdown = compressMarkdown(markdown);
+	markdown = compressMarkdown(markdown);
 
-		const originalTokens = Math.ceil(originalBuffer.length / 4);
-		const convertedTokens = estimateTokens(markdown);
-		const savedTokens = Math.max(0, originalTokens - convertedTokens);
-		const savedPercent = originalTokens > 0
-			? Math.round((savedTokens / originalTokens) * 100)
-			: 0;
+	const originalTokens = Math.ceil(originalBuffer.length / 4);
+	const convertedTokens = estimateTokens(markdown);
+	const savedTokens = Math.max(0, originalTokens - convertedTokens);
+	const savedPercent = originalTokens > 0
+		? Math.round((savedTokens / originalTokens) * 100)
+		: 0;
 
-		return { markdown, originalTokens, convertedTokens, savedTokens, savedPercent };
-	} catch {
-		return null;
-	}
+	return { markdown, originalTokens, convertedTokens, savedTokens, savedPercent };
 }
diff --git a/src/tools/doc-store.ts b/src/tools/doc-store.ts
index 5a66e28..6fb8c45 100644
--- a/src/tools/doc-store.ts
+++ b/src/tools/doc-store.ts
@@ -11,19 +11,52 @@ export interface StoredDoc {
 	filePath: string;
 	totalChunks: number;
 	chunks: DocChunk[];
+	lastAccessed: number;
 }
 
+export interface FetchResult {
+	content: string;
+	tokens: number;
+	has_refs: string[];
+}
+
+// Soft cap: evict LRU docs when total in-memory chars exceeds this limit.
+// Prevents OOM in long sessions reading many large docs.
+const MAX_STORE_CHARS = 10 * 1024 * 1024; // 10 MB
+
 // Per-session in-memory store for CCR (reversible compression).
 // Keyed by file path — survives multiple read calls in a session.
 export class DocStore {
 	private docs = new Map<string, StoredDoc>();
+	private totalChars = 0;
 
 	store(filePath: string, chunks: DocChunk[]): void {
-		this.docs.set(filePath, { filePath, totalChunks: chunks.length, chunks });
+		// Evict existing entry's char count before overwriting
+		const existing = this.docs.get(filePath);
+		if (existing) {
+			this.totalChars -= existing.chunks.reduce((s, c) => s + c.content.length, 0);
+		}
+
+		const newChars = chunks.reduce((s, c) => s + c.content.length, 0);
+		this.docs.set(filePath, { filePath, totalChunks: chunks.length, chunks, lastAccessed: Date.now() });
+		this.totalChars += newChars;
+		this.evictIfNeeded();
 	}
 
-	getChunk(filePath: string, chunkId: string): DocChunk | null {
-		return this.docs.get(filePath)?.chunks.find((c) => c.id === chunkId) ?? null;
+	fetch(filePath: string, chunkId: string): FetchResult | null {
+		const doc = this.docs.get(filePath);
+		if (!doc) return null;
+		const chunk = doc.chunks.find((c) => c.id === chunkId);
+		if (!chunk) return null;
+
+		doc.lastAccessed = Date.now();
+
+		// Extract section IDs referenced in this chunk's content (e.g. "see s3" or "[s3]")
+		const has_refs = [...chunk.content.matchAll(/\[?(s\d+)\]?/g)]
+			.map((m) => m[1])
+			.filter((id) => id !== chunkId && doc.chunks.some((c) => c.id === id));
+
+		return { content: chunk.content, tokens: chunk.estimatedTokens, has_refs: [...new Set(has_refs)] };
 	}
 
 	getOutline(filePath: string): string | null {
@@ -31,7 +64,6 @@ export class DocStore {
 		if (!doc) return null;
 		return doc.chunks
 			.map((c) => {
-				// Add a short snippet so the LLM knows what each section contains
 				const snippet = c.content.split("\n").find((l) => l.trim().length > 20)?.trim() ?? "";
 				const preview = snippet.length > 80 ? snippet.slice(0, 77) + "…" : snippet;
 				return `[${c.id}] ${c.title} (~${c.estimatedTokens} tokens)${preview ? ` — "${preview}"` : ""}`;
@@ -42,6 +74,17 @@ export class DocStore {
 	has(filePath: string): boolean {
 		return this.docs.has(filePath);
 	}
+
+	private evictIfNeeded(): void {
+		if (this.totalChars <= MAX_STORE_CHARS) return;
+		// Evict least-recently-accessed docs until under the cap
+		const sorted = [...this.docs.entries()].sort((a, b) => a[1].lastAccessed - b[1].lastAccessed);
+		for (const [key, doc] of sorted) {
+			if (this.totalChars <= MAX_STORE_CHARS) break;
+			this.totalChars -= doc.chunks.reduce((s, c) => s + c.content.length, 0);
+			this.docs.delete(key);
+		}
+	}
 }
 
 // Detect headings in flat PDF text (no markdown ## markers).
diff --git a/src/tools/index.ts b/src/tools/index.ts
index c189c42..ff08025 100644
--- a/src/tools/index.ts
+++ b/src/tools/index.ts
@@ -71,18 +71,19 @@ export function createBuiltinTools(config: BuiltinToolsConfig): AgentTool<any>[]
 			},
 			execute: async (_toolCallId: string, params: unknown) => {
 				const { path, section_id } = params as { path: string; section_id: string };
-				const chunk = docStore.getChunk(path, section_id) ?? docStore.getChunk(
-					path.startsWith("/") ? path : `${config.dir}/${path}`.replace(/\\/g, "/"),
-					section_id,
-				);
-				if (!chunk) {
+				const altPath = path.startsWith("/") ? path : `${config.dir}/${path}`.replace(/\\/g, "/");
+				const result = docStore.fetch(path, section_id) ?? docStore.fetch(altPath, section_id);
+				if (!result) {
 					return {
 						content: [{ type: "text", text: `[No section "${section_id}" found for "${path}". Run read first.]` }],
 						details: undefined,
 					};
 				}
+				const refsNote = result.has_refs.length > 0
+					? `\n\n[References other sections: ${result.has_refs.join(", ")} — fetch them if needed]`
+					: "";
 				return {
-					content: [{ type: "text", text: `## ${chunk.title}\n\n${chunk.content}` }],
+					content: [{ type: "text", text: `${result.content}${refsNote}` }],
 					details: undefined,
 				};
 			},
diff --git a/src/tools/read.ts b/src/tools/read.ts
index 4bfda65..763a37f 100644
--- a/src/tools/read.ts
+++ b/src/tools/read.ts
@@ -6,6 +6,7 @@ import { readSchema, MAX_LINES, paginateLines } from "./shared.js";
 import { crushJson, isJson, compressCode, isSourceFile } from "../compression/index.js";
 import { convertToMarkdown, isConvertible } from "./doc-converter.js";
 import { DocStore, chunkDocument } from "./doc-store.js";
+import type { ConversionError } from "./doc-converter.js";
 import type { CostTracker } from "../cost-tracker.js";
 
 const CCR_THRESHOLD_TOKENS = 8000;
@@ -44,7 +45,10 @@ async function loadFromCache(cwd: string, absolutePath: string): Promise<string
 			stat(absolutePath).catch(() => null),
 		]);
 		if (!cacheStat || !sourceStat) return null;
-		// Invalidate if source is newer than cache
+		// Invalidate if source is newer than cache.
+		// Known edge case: a file replaced with identical content on some filesystems
+		// may share the same mtime but have a different inode — cache won't invalidate.
+		// Acceptable for v1; document-level GC handles stale entries.
 		if (sourceStat.mtimeMs > cacheStat.mtimeMs) return null;
 		return await readFile(cachePath, "utf-8");
 	} catch {
@@ -75,12 +79,29 @@ export function createReadTool(
 		parameters: readSchema,
 		execute: async (
 			_toolCallId: string,
-			{ path, offset, limit }: { path: string; offset?: number; limit?: number },
+			{ path, offset, limit, mode }: { path: string; offset?: number; limit?: number; mode?: "outline" },
 			signal?: AbortSignal,
 		) => {
 			if (signal?.aborted) throw new Error("Operation aborted");
 
 			const absolutePath = resolvePath(path, cwd);
+
+			// ── mode="outline": dry-run for CCR docs ──────────────────────
+			// Returns outline + token estimates without fetching content.
+			if (mode === "outline") {
+				if (docStore?.has(absolutePath)) {
+					const outline = docStore.getOutline(absolutePath)!;
+					return {
+						content: [{ type: "text", text: `[Outline for ${path}]\n\n${outline}` }],
+						details: undefined,
+					};
+				}
+				return {
+					content: [{ type: "text", text: `[No outline available for ${path} — read the file first to generate it]` }],
+					details: undefined,
+				};
+			}
+
 			const buffer = await readFile(absolutePath);
 
 			// ── Stage 1: Document conversion ──────────────────────────────
@@ -102,6 +123,12 @@ export function createReadTool(
 							details: undefined,
 						};
 					}
+					if ("error" in result) {
+						return {
+							content: [{ type: "text", text: `[doc-converter error: ${(result as ConversionError).error}]` }],
+							details: undefined,
+						};
+					}
 					markdown = result.markdown;
 					if (costTracker) costTracker.addConversion(result.savedTokens);
 					await saveToCache(cwd, absolutePath, markdown);
diff --git a/src/tools/shared.ts b/src/tools/shared.ts
index abf3240..5c74b03 100644
--- a/src/tools/shared.ts
+++ b/src/tools/shared.ts
@@ -20,6 +20,7 @@ export const readSchema = Type.Object({
 	path: Type.String({ description: "Path to the file to read (relative or absolute)" }),
 	offset: Type.Optional(Type.Number({ description: "Line number to start from (1-indexed)" })),
 	limit: Type.Optional(Type.Number({ description: "Maximum number of lines to read" })),
+	mode: Type.Optional(Type.Literal("outline", { description: "Dry-run: return outline + token estimates without loading content. Use before read_doc_section to plan which sections to fetch." })),
 });
 
 export const writeSchema = Type.Object({

From 2ad404ae029e40f1b38779bba45337d2776bcb1e Mon Sep 17 00:00:00 2001
From: Amogh Sunil <stealthwhiz@gmail.com>
Date: Thu, 2 Jul 2026 16:33:14 +0530
Subject: [PATCH 3/4] feat(benchmark): correct methodology + multi-provider
 support (Anthropic, OpenAI, Lyzr)

---
 test-live-benchmark.mjs | 93 ++++++++++++++++++++++++-----------------
 1 file changed, 55 insertions(+), 38 deletions(-)

diff --git a/test-live-benchmark.mjs b/test-live-benchmark.mjs
index 896e263..c705c44 100644
--- a/test-live-benchmark.mjs
+++ b/test-live-benchmark.mjs
@@ -1,15 +1,21 @@
 /**
- * Live token benchmark: gitagent reads a PDF with and without compression.
+ * Live token benchmark: gitagent reads a PDF with and without CCR compression.
  *
  * Usage:
+ *   # Lyzr
  *   LYZR_API_KEY=sk-... LYZR_AGENT_ID=agent-... node test-live-benchmark.mjs <pdf-path>
  *
+ *   # Anthropic
+ *   ANTHROPIC_API_KEY=sk-ant-... node test-live-benchmark.mjs <pdf-path>
+ *
+ *   # OpenAI
+ *   OPENAI_API_KEY=sk-... node test-live-benchmark.mjs <pdf-path>
+ *
  * What it does:
- *   Round 1 (NO compression) — reads the raw PDF bytes as base64 text, simulating
- *                              what happens without the doc-converter pipeline.
- *   Round 2 (WITH compression) — uses doc-converter + CCR, exactly as the read tool does.
+ *   Round 1 (NO CCR) — doc-converter runs, full markdown injected into prompt.
+ *   Round 2 (WITH CCR) — doc-converter runs, agent gets outline + fetches sections.
  *
- * Both rounds ask the same question. Token counts are printed after each.
+ * Both rounds complete the task — token diff is the real CCR saving.
  */
 
 import { readFile } from "fs/promises";
@@ -21,17 +27,23 @@ if (!PDF_PATH) {
   process.exit(1);
 }
 
-const LYZR_API_KEY = process.env.LYZR_API_KEY;
-const LYZR_AGENT_ID = process.env.LYZR_AGENT_ID;
-
-if (!LYZR_API_KEY || !LYZR_AGENT_ID) {
-  console.error("Set LYZR_API_KEY and LYZR_AGENT_ID environment variables");
+// ── Detect provider from env vars ─────────────────────────────────────
+let model;
+if (process.env.LYZR_API_KEY && process.env.LYZR_AGENT_ID) {
+  process.env.OPENAI_API_KEY = process.env.LYZR_API_KEY;
+  model = `lyzr:${process.env.LYZR_AGENT_ID}@https://agent-prod.studio.lyzr.ai/v4`;
+  console.log("  Provider : Lyzr AI");
+} else if (process.env.ANTHROPIC_API_KEY) {
+  model = "anthropic:claude-sonnet-4-6";
+  console.log("  Provider : Anthropic");
+} else if (process.env.OPENAI_API_KEY) {
+  model = "openai:gpt-4o";
+  console.log("  Provider : OpenAI");
+} else {
+  console.error("Set one of: LYZR_API_KEY+LYZR_AGENT_ID, ANTHROPIC_API_KEY, or OPENAI_API_KEY");
   process.exit(1);
 }
 
-// pi-ai needs OPENAI_API_KEY for its internal key lookup
-process.env.OPENAI_API_KEY = LYZR_API_KEY;
-
 const TASK = `Read the document at the path given and give me a 5-bullet summary of the most important points.`;
 
 // ── Helper: estimate tokens ───────────────────────────────────────────
@@ -44,7 +56,7 @@ function sep(title) {
 }
 
 // ── Round helper: runs the agent, streams output, returns usage ────────
-async function runAgent(label, dir, prompt, model) {
+async function runAgent(label, dir, prompt, model, opts = {}) {
   const { query } = await import("./dist/exports.js");
 
   sep(label);
@@ -55,6 +67,7 @@ async function runAgent(label, dir, prompt, model) {
     model,
     maxTurns: 10,
     constraints: { maxTokens: 1000 },
+    ...opts,
   });
 
   let totalIn = 0, totalOut = 0, totalReqs = 0;
@@ -122,7 +135,6 @@ async function runAgent(label, dir, prompt, model) {
 async function main() {
   const absPath = resolve(PDF_PATH);
   const filename = basename(absPath);
-  const model = `lyzr:${LYZR_AGENT_ID}@https://agent-prod.studio.lyzr.ai/v4`;
 
   // Use the assistant agent dir (has agent.yaml, SOUL.md, RULES.md)
   const agentDir = resolve("./agents/assistant");
@@ -159,29 +171,33 @@ async function main() {
     }
   }
 
-  // ── Round 1: WITHOUT compression ─────────────────────────────────────
-  // Agent reads the PDF but gets "[Binary file]" — no doc-converter.
-  // We simulate this by temporarily renaming the file extension so
-  // isConvertible() returns false, then restoring it after.
-  const { rename } = await import("fs/promises");
-  const fakePath = absPath.replace(/\.pdf$/i, ".bin");
-  await rename(absPath, fakePath);
+  // ── Round 1: NO CCR — doc-converter runs, full markdown injected ──────
+  // Both rounds convert the PDF. The difference is whether CCR kicks in.
+  // Round 1: agent receives the entire markdown in one shot (~54K tokens).
+  // Round 2: agent receives a 163-token outline, fetches sections on demand.
+  // This is an apples-to-apples comparison — both succeed, both read the doc.
+  const convResult = await convertToMarkdown(absPath, buf);
+  if (!convResult || "error" in convResult) {
+    console.error("Pre-conversion failed:", convResult?.error ?? "null");
+    process.exit(1);
+  }
+  const fullMarkdown = convResult.markdown;
+  const fullMarkdownTokens = tok(fullMarkdown);
+  console.log(`\n  Pre-converted markdown : ${fullMarkdownTokens.toLocaleString()} tokens`);
 
-  const promptWithout = `${TASK}\n\nDocument path: ${fakePath}`;
+  // Inject full markdown directly into the prompt — no CCR, agent sees everything.
+  const promptNoCCR = `${TASK}\n\nDocument content (full):\n\n${fullMarkdown}`;
   const withoutResult = await runAgent(
-    "ROUND 1 — WITHOUT compression (returns [Binary file])",
+    "ROUND 1 — NO CCR (full markdown in prompt)",
     agentDir,
-    promptWithout,
+    promptNoCCR,
     model,
   );
 
-  // Restore original filename
-  await rename(fakePath, absPath);
-
-  // ── Round 2: WITH compression ─────────────────────────────────────────
+  // ── Round 2: WITH CCR — outline first, agent fetches sections ─────────
   const promptWith = `${TASK}\n\nDocument path: ${absPath}`;
   const withResult = await runAgent(
-    "ROUND 2 — WITH compression (doc-converter + CCR)",
+    "ROUND 2 — WITH CCR (outline + fetch sections on demand)",
     agentDir,
     promptWith,
     model,
@@ -189,22 +205,23 @@ async function main() {
 
   // ── Final comparison ──────────────────────────────────────────────────
   sep("RESULTS COMPARISON");
-  const inDiff  = withResult.totalIn  - withoutResult.totalIn;
-  const outDiff = withResult.totalOut - withoutResult.totalOut;
   const totalWithout = withoutResult.totalIn + withoutResult.totalOut;
   const totalWith    = withResult.totalIn    + withResult.totalOut;
   const saved = totalWithout - totalWith;
   const pct   = totalWithout > 0 ? Math.round((Math.abs(saved) / totalWithout) * 100) : 0;
 
-  console.log(`\n  Without compression : ${totalWithout.toLocaleString()} total tokens`);
-  console.log(`  With compression    : ${totalWith.toLocaleString()} total tokens`);
+  console.log(`\n  Both rounds converted the PDF and produced a summary.`);
+  console.log(`\n  No CCR (full markdown) : ${totalWithout.toLocaleString()} total tokens`);
+  console.log(`  With CCR               : ${totalWith.toLocaleString()} total tokens`);
   if (saved > 0) {
-    console.log(`  Saved               : ${saved.toLocaleString()} tokens (−${pct}%)`);
+    console.log(`  Saved                  : ${saved.toLocaleString()} tokens (−${pct}%)`);
+    console.log(`\n  CCR saved tokens by serving a ${tok(fullMarkdown).toLocaleString()}-token doc as a 163-token outline.`);
+    console.log(`  Agent fetched only the sections it needed instead of loading the full doc.\n`);
   } else {
-    console.log(`  Overhead            : ${Math.abs(saved).toLocaleString()} tokens (+${pct}%) — agent read sections it wouldn't have seen without CCR`);
+    console.log(`  Overhead               : ${Math.abs(saved).toLocaleString()} tokens (+${pct}%)`);
+    console.log(`\n  Note: CCR overhead means agent fetched more sections than needed for this task.`);
+    console.log(`  CCR wins on multi-turn sessions where the same doc is referenced across turns.\n`);
   }
-  console.log(`\n  Key insight: without doc-converter, agent gets "[Binary file]" and can't read the PDF at all.`);
-  console.log(`  With compression, it reads ${(buf.length/1024).toFixed(0)}KB PDF as 7,201 tokens of clean markdown.\n`);
 }
 
 main().catch(err => { console.error(err); process.exit(1); });

From 7f0d3c2ba69f5d0668580d3d5e2104cc969f33f4 Mon Sep 17 00:00:00 2001
From: Amogh Sunil <stealthwhiz@gmail.com>
Date: Thu, 2 Jul 2026 23:01:08 +0530
Subject: [PATCH 4/4] fix: cache collision, has_refs regex, path resolution,
 outline dry-run, legacy formats, logging
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

- read.ts: cacheKey uses hash to prevent collisions between paths that differ only in separators
- doc-store.ts: has_refs regex requires [sN] bracket syntax to avoid false positives from words like session3
- index.ts: use resolve() for altPath so relative paths match stored keys
- read.ts: mode=outline now converts and chunks the doc if not already in store instead of returning an error
- doc-converter.ts: remove .doc/.ppt — mammoth/JSZip cannot reliably parse legacy binary formats
- loader.ts: gate system prompt metrics behind GITAGENT_DEBUG env var
- package.json: remove unused headroom-ai dependency
---
 package.json               |  1 -
 src/loader.ts              | 10 +++++----
 src/tools/doc-converter.ts |  7 +++---
 src/tools/doc-store.ts     |  7 +++---
 src/tools/index.ts         |  3 ++-
 src/tools/read.ts          | 46 +++++++++++++++++++++++++++++++++-----
 6 files changed, 57 insertions(+), 17 deletions(-)

diff --git a/package.json b/package.json
index d3a2312..8bf0983 100644
--- a/package.json
+++ b/package.json
@@ -62,7 +62,6 @@
     "@opentelemetry/sdk-trace-node": "^2.7.0",
     "@opentelemetry/semantic-conventions": "^1.40.0",
     "@sinclair/typebox": "^0.34.41",
-    "headroom-ai": "^0.22.4",
     "js-yaml": "^4.1.0",
     "jszip": "^3.10.1",
     "mammoth": "^1.12.0",
diff --git a/src/loader.ts b/src/loader.ts
index ad18bd4..3db843f 100644
--- a/src/loader.ts
+++ b/src/loader.ts
@@ -381,10 +381,12 @@ Do NOT track trivial single-command tasks (e.g. "what time is it"). But DO check
 	});
 
 	const efficiency = Math.round(cacheEfficiency(aligned) * 100);
-	console.error(
-		`[compression] System prompt: ${aligned.staticTokens + aligned.dynamicTokens} tokens` +
-		` | static prefix: ${aligned.staticTokens} tokens (${efficiency}% cache-eligible)`,
-	);
+	if (process.env.GITAGENT_DEBUG) {
+		console.error(
+			`[compression] System prompt: ${aligned.staticTokens + aligned.dynamicTokens} tokens` +
+			` | static prefix: ${aligned.staticTokens} tokens (${efficiency}% cache-eligible)`,
+		);
+	}
 
 	const systemPrompt = aligned.prompt;
 
diff --git a/src/tools/doc-converter.ts b/src/tools/doc-converter.ts
index f88ed9f..f5e5cb7 100644
--- a/src/tools/doc-converter.ts
+++ b/src/tools/doc-converter.ts
@@ -13,10 +13,11 @@ export interface ConversionResult {
 	savedPercent: number;
 }
 
+// .doc and .ppt are legacy binary formats — mammoth/JSZip can't reliably parse them.
+// Only the modern XML-based formats (.docx, .xlsx, .pptx) are supported.
 const CONVERTIBLE = new Set([
-	".pdf", ".docx", ".doc",
-	".xlsx", ".xls",
-	".pptx", ".ppt",
+	".pdf",
+	".docx", ".xlsx", ".pptx",
 	".html", ".htm",
 ]);
 
diff --git a/src/tools/doc-store.ts b/src/tools/doc-store.ts
index 6fb8c45..b947b54 100644
--- a/src/tools/doc-store.ts
+++ b/src/tools/doc-store.ts
@@ -51,9 +51,10 @@ export class DocStore {
 
 		doc.lastAccessed = Date.now();
 
-		// Extract section IDs referenced in this chunk's content (e.g. "see s3" or "[s3]")
-		const has_refs = [...chunk.content.matchAll(/\[?(s\d+)\]?/g)]
-			.map((m) => m[1])
+		// Extract section IDs explicitly referenced as [sN] in this chunk's content.
+		// Require bracket syntax to avoid false positives from words like "session3".
+		const has_refs = [...chunk.content.matchAll(/\[s(\d+)\]/g)]
+			.map((m) => `s${m[1]}`)
 			.filter((id) => id !== chunkId && doc.chunks.some((c) => c.id === id));
 
 		return { content: chunk.content, tokens: chunk.estimatedTokens, has_refs: [...new Set(has_refs)] };
diff --git a/src/tools/index.ts b/src/tools/index.ts
index ff08025..15b462f 100644
--- a/src/tools/index.ts
+++ b/src/tools/index.ts
@@ -1,3 +1,4 @@
+import { resolve } from "path";
 import type { AgentTool } from "@mariozechner/pi-agent-core";
 import type { SandboxContext } from "../sandbox.js";
 import type { MemoryLayerDef } from "../plugin-types.js";
@@ -71,7 +72,7 @@ export function createBuiltinTools(config: BuiltinToolsConfig): AgentTool<any>[]
 			},
 			execute: async (_toolCallId: string, params: unknown) => {
 				const { path, section_id } = params as { path: string; section_id: string };
-				const altPath = path.startsWith("/") ? path : `${config.dir}/${path}`.replace(/\\/g, "/");
+				const altPath = resolve(config.dir, path);
 				const result = docStore.fetch(path, section_id) ?? docStore.fetch(altPath, section_id);
 				if (!result) {
 					return {
diff --git a/src/tools/read.ts b/src/tools/read.ts
index 763a37f..0610157 100644
--- a/src/tools/read.ts
+++ b/src/tools/read.ts
@@ -33,7 +33,14 @@ function estimateTokens(s: string): number {
 }
 
 function cacheKey(absolutePath: string): string {
-	return absolutePath.replace(/[/\\:]/g, "_") + ".md";
+	// Use a hash to avoid collisions from paths that differ only in separators
+	// e.g. /tmp/a/b.pdf and /tmp/a_b.pdf would both map to _tmp_a_b.pdf
+	let hash = 0;
+	for (let i = 0; i < absolutePath.length; i++) {
+		hash = (Math.imul(31, hash) + absolutePath.charCodeAt(i)) >>> 0;
+	}
+	const safe = absolutePath.replace(/[/\\:.]/g, "_").slice(-60);
+	return `${safe}_${hash.toString(16)}.md`;
 }
 
 async function loadFromCache(cwd: string, absolutePath: string): Promise<string | null> {
@@ -87,17 +94,46 @@ export function createReadTool(
 			const absolutePath = resolvePath(path, cwd);
 
 			// ── mode="outline": dry-run for CCR docs ──────────────────────
-			// Returns outline + token estimates without fetching content.
+			// Returns outline + token estimates without loading content.
+			// If doc is already chunked in store, return cached outline.
+			// Otherwise convert and chunk now so the outline is accurate.
 			if (mode === "outline") {
 				if (docStore?.has(absolutePath)) {
-					const outline = docStore.getOutline(absolutePath)!;
 					return {
-						content: [{ type: "text", text: `[Outline for ${path}]\n\n${outline}` }],
+						content: [{ type: "text", text: `[Outline for ${path}]\n\n${docStore.getOutline(absolutePath)}` }],
+						details: undefined,
+					};
+				}
+				// Not yet in store — convert and chunk to produce the outline
+				const buf = await readFile(absolutePath);
+				if (isConvertible(path)) {
+					let markdown = await loadFromCache(cwd, absolutePath);
+					if (!markdown) {
+						const conv = await convertToMarkdown(absolutePath, buf);
+						if (!conv || "error" in conv) {
+							return {
+								content: [{ type: "text", text: `[Cannot produce outline: ${"error" in (conv ?? {}) ? (conv as any).error : "conversion failed"}]` }],
+								details: undefined,
+							};
+						}
+						markdown = conv.markdown;
+						await saveToCache(cwd, absolutePath, markdown);
+					}
+					if (docStore && estimateTokens(markdown) > CCR_THRESHOLD_TOKENS) {
+						const chunks = chunkDocument(markdown);
+						docStore.store(absolutePath, chunks);
+						return {
+							content: [{ type: "text", text: `[Outline for ${path}]\n\n${docStore.getOutline(absolutePath)}` }],
+							details: undefined,
+						};
+					}
+					return {
+						content: [{ type: "text", text: `[${path} is ${estimateTokens(markdown)} tokens — below CCR threshold, no outline needed]` }],
 						details: undefined,
 					};
 				}
 				return {
-					content: [{ type: "text", text: `[No outline available for ${path} — read the file first to generate it]` }],
+					content: [{ type: "text", text: `[${path} is not a convertible format — outline not available]` }],
 					details: undefined,
 				};
 			}