diff --git a/package.json b/package.json
index 05b77509f..d7eaa7e8f 100644
--- a/package.json
+++ b/package.json
@@ -112,6 +112,7 @@
 		"clsx": "^2.1.1",
 		"drizzle-kit": "^0.31.10",
 		"drizzle-orm": "^0.45.2",
+		"fflate": "^0.8.3",
 		"hast-util-to-string": "^3.0.1",
 		"katex": "^0.17.0",
 		"linkedom": "0.18.13",
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 5eb56efb5..03e892521 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -236,6 +236,9 @@ importers:
       drizzle-orm:
         specifier: ^0.45.2
         version: 0.45.2(@cloudflare/workers-types@5.20260801.1)(@opentelemetry/api@1.9.1)(@types/pg@8.20.0)(kysely@0.29.4)(pg@8.22.0)(sql.js@1.14.1)
+      fflate:
+        specifier: ^0.8.3
+        version: 0.8.3
       hast-util-to-string:
         specifier: ^3.0.1
         version: 3.0.1
@@ -6225,6 +6228,9 @@ packages:
   fflate@0.4.9:
     resolution: {integrity: sha512-zdxgIEddhfsyCaWpJ2SdXEP8ZMrKJ6+5jl4OupODcywU0IhRk6gdXuVGcPICyfx2H97hVK7xmJtRLPjkxAX8Vw==}
 
+  fflate@0.8.3:
+    resolution: {integrity: sha512-tbZNuJrLwGUp3zshBtdy4W+ORxZuIh8a5ilyIEQDC5rY1f3U20JMry0Ll3WBzU58EZKsEuJFXhb5gwv8CsPvgA==}
+
   figures@6.1.0:
     resolution: {integrity: sha512-d+l3qxjSesT4V7v2fh+QnmFnUWv9lSpjarhShNTgBOfA0ttejbQUAlHLitbjkoRiDulW0OPoQPYIGhIC8ohejg==}
     engines: {node: '>=18'}
@@ -14685,6 +14691,8 @@ snapshots:
 
   fflate@0.4.9: {}
 
+  fflate@0.8.3: {}
+
   figures@6.1.0:
     dependencies:
       is-unicode-supported: 2.1.0
diff --git a/src/features/workspaces/ai/ai-thread.ts b/src/features/workspaces/ai/ai-thread.ts
index e4da44214..9300ea65d 100644
--- a/src/features/workspaces/ai/ai-thread.ts
+++ b/src/features/workspaces/ai/ai-thread.ts
@@ -131,10 +131,6 @@ export function createAIThreadClass(getUserAIStore: () => typeof UserAIStore) {
 			);
 		}
 
-		getSystemPrompt(): string {
-			return getAIThreadSoulPrompt();
-		}
-
 		// On-demand instruction bundles (progressive disclosure). The model sees
 		// only each skill's name/description until a task matches, then calls
 		// activate_skill to load the full guide. Bundled from ./skills via the
diff --git a/src/features/workspaces/components/WorkspaceContextBar.tsx b/src/features/workspaces/components/WorkspaceContextBar.tsx
index 168092d69..9f75cf64f 100644
--- a/src/features/workspaces/components/WorkspaceContextBar.tsx
+++ b/src/features/workspaces/components/WorkspaceContextBar.tsx
@@ -1,5 +1,6 @@
-import { ChevronDown, Clock3, Settings, Share2 } from "lucide-react";
+import { ChevronDown, Clock3, Download, Settings, Share2 } from "lucide-react";
 import { type ComponentType, type ReactElement, useState } from "react";
+import { toast } from "sonner";
 
 import {
 	Breadcrumb,
@@ -94,6 +95,14 @@ export default function WorkspaceContextBar({
 	const workspaceItems = Array.from(itemsById.values());
 	const searchHotkey = formatAppHotkey(getAppHotkey("workspace.search.open").hotkey);
 	const openWorkspaceSearch = () => setSearchOpen(true);
+	const exportWorkspace = () => {
+		toast.message("Preparing workspace export…");
+		const link = document.createElement("a");
+		link.href = `/api/v1/workspaces/${encodeURIComponent(workspace.id)}/export`;
+		link.target = "_blank";
+		link.rel = "noopener";
+		link.click();
+	};
 
 	useAppHotkey("workspace.search.open", () => {
 		openWorkspaceSearch();
@@ -117,6 +126,7 @@ export default function WorkspaceContextBar({
 							) : (
 								<WorkspaceRootActionsMenu
 									capabilities={capabilities}
+									onExport={exportWorkspace}
 									onOpenSettings={() => setSettingsOpen(true)}
 									onOpenShare={() => setShareOpen(true)}
 									trigger={
@@ -221,11 +231,13 @@ export default function WorkspaceContextBar({
 
 function WorkspaceRootActionsMenu({
 	capabilities,
+	onExport,
 	onOpenSettings,
 	onOpenShare,
 	trigger,
 }: {
 	capabilities: ReturnType<typeof useWorkspaceMutationAccess>["capabilities"];
+	onExport: () => void;
 	onOpenSettings: () => void;
 	onOpenShare: () => void;
 	trigger: ReactElement;
@@ -237,6 +249,7 @@ function WorkspaceRootActionsMenu({
 				{renderWorkspaceMenuActions(
 					getWorkspaceRootMenuActions({
 						canOpenSettings: capabilities.canMutateContent,
+						onExport,
 						onOpenSettings,
 						onOpenShare,
 					}),
@@ -249,6 +262,7 @@ function WorkspaceRootActionsMenu({
 
 function getWorkspaceRootMenuActions(input: {
 	canOpenSettings: boolean;
+	onExport: () => void;
 	onOpenSettings: () => void;
 	onOpenShare: () => void;
 }): WorkspaceMenuAction[] {
@@ -268,6 +282,13 @@ function getWorkspaceRootMenuActions(input: {
 			trailing: "Soon",
 			disabled: true,
 		},
+		{
+			kind: "item",
+			id: "export",
+			label: "Export",
+			leading: <Download className="size-4" />,
+			onSelect: input.onExport,
+		},
 		{
 			kind: "item",
 			id: "settings",
diff --git a/src/features/workspaces/contracts.ts b/src/features/workspaces/contracts.ts
index 3f82a6408..e36f52ea1 100644
--- a/src/features/workspaces/contracts.ts
+++ b/src/features/workspaces/contracts.ts
@@ -8,6 +8,8 @@ import {
 export { workspaceItemTypeSchema };
 export type { WorkspaceItemType };
 
+export const WORKSPACE_ITEM_NAME_MAX_LENGTH = 160;
+
 export type JsonValue =
 	| string
 	| number
@@ -226,7 +228,7 @@ export const createWorkspaceItemInputSchema = z
 		workspaceId: z.string().min(1),
 		parentId: z.string().min(1).nullable().optional(),
 		type: workspaceItemTypeSchema,
-		name: z.string().trim().min(1).max(160).optional(),
+		name: z.string().trim().min(1).max(WORKSPACE_ITEM_NAME_MAX_LENGTH).optional(),
 		color: workspaceColorSchema.optional(),
 		initialContent: z.string().optional(),
 		clientMutationId: z.uuid().optional(),
@@ -244,7 +246,7 @@ export const createWorkspaceItemInputSchema = z
 export const renameWorkspaceItemInputSchema = z.object({
 	workspaceId: z.string().min(1),
 	itemId: z.string().min(1),
-	name: z.string().trim().min(1).max(160),
+	name: z.string().trim().min(1).max(WORKSPACE_ITEM_NAME_MAX_LENGTH),
 	clientMutationId: z.uuid().optional(),
 });
 
diff --git a/src/features/workspaces/defaults.test.ts b/src/features/workspaces/defaults.test.ts
new file mode 100644
index 000000000..82603e00c
--- /dev/null
+++ b/src/features/workspaces/defaults.test.ts
@@ -0,0 +1,24 @@
+import { describe, expect, it } from "vitest";
+
+import {
+	getAvailableWorkspaceItemName,
+	normalizeWorkspaceItemName,
+} from "#/features/workspaces/defaults";
+
+describe("workspace item names", () => {
+	it("normalizes names for portable filesystem paths", () => {
+		expect(normalizeWorkspaceItemName("  Notes: draft?.md.  ")).toBe("Notes- draft-.md");
+		expect(normalizeWorkspaceItemName("..")).toBe("Untitled");
+		expect(normalizeWorkspaceItemName("CON.txt")).toBe("_CON.txt");
+	});
+
+	it("allocates sibling names case-insensitively", () => {
+		expect(
+			getAvailableWorkspaceItemName({
+				type: "folder",
+				existingNames: ["Notes"],
+				requestedName: "notes",
+			}),
+		).toBe("notes 2");
+	});
+});
diff --git a/src/features/workspaces/defaults.ts b/src/features/workspaces/defaults.ts
index 526e8d607..af25a5fb7 100644
--- a/src/features/workspaces/defaults.ts
+++ b/src/features/workspaces/defaults.ts
@@ -1,7 +1,8 @@
-import type {
-	WorkspaceColor,
-	WorkspaceIcon,
-	WorkspaceItemType,
+import {
+	WORKSPACE_ITEM_NAME_MAX_LENGTH,
+	type WorkspaceColor,
+	type WorkspaceIcon,
+	type WorkspaceItemType,
 } from "#/features/workspaces/contracts";
 import { getWorkspaceItemRegistryEntry } from "#/features/workspaces/workspace-item-registry";
 
@@ -27,9 +28,9 @@ export function getAvailableWorkspaceItemName(input: {
 		? normalizeWorkspaceItemName(input.requestedName, "")
 		: "";
 	const baseName = requestedName || getDefaultWorkspaceItemName(input.type);
-	const existingNames = new Set(input.existingNames);
+	const existingNames = new Set(Array.from(input.existingNames, getWorkspaceItemNameKey));
 
-	if (requestedName && !existingNames.has(baseName)) {
+	if (requestedName && !existingNames.has(getWorkspaceItemNameKey(baseName))) {
 		return baseName;
 	}
 
@@ -37,7 +38,7 @@ export function getAvailableWorkspaceItemName(input: {
 		for (let suffix = 1; suffix < 1000; suffix += 1) {
 			const candidate = `${baseName} ${suffix}`;
 
-			if (!existingNames.has(candidate)) {
+			if (!existingNames.has(getWorkspaceItemNameKey(candidate))) {
 				return candidate;
 			}
 		}
@@ -48,7 +49,7 @@ export function getAvailableWorkspaceItemName(input: {
 	for (let suffix = 2; suffix < 1000; suffix += 1) {
 		const candidate = `${baseName} ${suffix}`;
 
-		if (!existingNames.has(candidate)) {
+		if (!existingNames.has(getWorkspaceItemNameKey(candidate))) {
 			return candidate;
 		}
 	}
@@ -59,13 +60,25 @@ export function getAvailableWorkspaceItemName(input: {
 export function normalizeWorkspaceItemName(name: string | null | undefined, fallback = "Untitled") {
 	const normalized =
 		stripControlCharacters(name ?? "")
-			.replace(/[\\/]+/g, "-")
+			.normalize("NFC")
+			.replace(/[<>:"/\\|?*]+/g, "-")
 			.replace(/\s+/g, " ")
 			.trim()
-			.slice(0, 160)
-			.trim() ?? "";
+			.slice(0, WORKSPACE_ITEM_NAME_MAX_LENGTH)
+			.trim()
+			.replace(/[. ]+$/g, "") ?? "";
+
+	if (!normalized) {
+		return fallback;
+	}
+
+	return /^(?:con|prn|aux|nul|com[1-9]|lpt[1-9])(?:\.|$)/i.test(normalized)
+		? `_${normalized}`.slice(0, WORKSPACE_ITEM_NAME_MAX_LENGTH)
+		: normalized;
+}
 
-	return normalized || fallback;
+export function getWorkspaceItemNameKey(name: string) {
+	return name.normalize("NFC").toLowerCase();
 }
 
 function stripControlCharacters(value: string) {
diff --git a/src/features/workspaces/export/workspace-export-archive.test.ts b/src/features/workspaces/export/workspace-export-archive.test.ts
new file mode 100644
index 000000000..851b81a2f
--- /dev/null
+++ b/src/features/workspaces/export/workspace-export-archive.test.ts
@@ -0,0 +1,108 @@
+import { strFromU8, unzipSync } from "fflate";
+import { describe, expect, it, vi } from "vitest";
+
+import type { WorkspaceItemSummary } from "#/features/workspaces/contracts";
+import { createWorkspaceExportStream } from "#/features/workspaces/export/workspace-export-archive";
+
+const baseItem = {
+	workspaceId: "workspace-1",
+	meta: "",
+	color: null,
+	metadataJson: {},
+	sortOrder: 0,
+	createdAt: "2026-08-05T00:00:00.000Z",
+	updatedAt: "2026-08-05T00:00:00.000Z",
+	deletedAt: null,
+} as const;
+
+describe("workspace export archive", () => {
+	it("preserves folders, converts documents to Markdown, and streams original files", async () => {
+		const items: WorkspaceItemSummary[] = [
+			{
+				...baseItem,
+				id: "folder",
+				parentId: null,
+				type: "folder",
+				title: "Research",
+				name: "Research",
+			},
+			{
+				...baseItem,
+				id: "document",
+				parentId: "folder",
+				type: "document",
+				title: "Notes",
+				name: "Notes",
+			},
+			{
+				...baseItem,
+				id: "file",
+				parentId: "folder",
+				type: "file",
+				title: "source.pdf",
+				name: "source.pdf",
+			},
+			{ ...baseItem, id: "empty", parentId: null, type: "folder", title: "Empty", name: "Empty" },
+		];
+		const archive = await new Response(
+			createWorkspaceExportStream(items, {
+				readDocument: vi.fn().mockReturnValue({
+					type: "doc",
+					content: [{ type: "paragraph", content: [{ type: "text", text: "Hello" }] }],
+				}),
+				readFile: vi.fn().mockResolvedValue(new Blob(["PDF bytes"]).stream()),
+			}),
+		).arrayBuffer();
+		const files = unzipSync(new Uint8Array(archive));
+
+		expect(Object.keys(files).sort()).toEqual([
+			"Empty/",
+			"Research/",
+			"Research/Notes.md",
+			"Research/source.pdf",
+		]);
+		expect(strFromU8(files["Research/Notes.md"]!)).toBe("Hello\n");
+		expect(strFromU8(files["Research/source.pdf"]!)).toBe("PDF bytes");
+	});
+
+	it("keeps every item when Markdown extensions collide", async () => {
+		const items: WorkspaceItemSummary[] = [
+			{
+				...baseItem,
+				id: "document-1",
+				parentId: null,
+				type: "document",
+				title: "Notes",
+				name: "Notes",
+			},
+			{
+				...baseItem,
+				id: "document-2",
+				parentId: null,
+				type: "document",
+				title: "Notes.md",
+				name: "Notes.md",
+			},
+			{
+				...baseItem,
+				id: "file",
+				parentId: null,
+				type: "file",
+				title: "notes.md",
+				name: "notes.md",
+			},
+		];
+		const archive = await new Response(
+			createWorkspaceExportStream(items, {
+				readDocument: vi.fn().mockReturnValue({ type: "doc" }),
+				readFile: vi.fn().mockResolvedValue(new Blob(["file"]).stream()),
+			}),
+		).arrayBuffer();
+
+		expect(Object.keys(unzipSync(new Uint8Array(archive))).sort()).toEqual([
+			"Notes (2).md",
+			"Notes (3).md",
+			"notes.md",
+		]);
+	});
+});
diff --git a/src/features/workspaces/export/workspace-export-archive.ts b/src/features/workspaces/export/workspace-export-archive.ts
new file mode 100644
index 000000000..a0113815f
--- /dev/null
+++ b/src/features/workspaces/export/workspace-export-archive.ts
@@ -0,0 +1,167 @@
+import { Zip, ZipPassThrough } from "fflate";
+
+import type { WorkspaceItemSummary } from "#/features/workspaces/contracts";
+import { serializeTiptapDocumentToMarkdown } from "#/features/workspaces/documents/document-markdown";
+import type { TiptapDocumentJson } from "#/features/workspaces/documents/tiptap-document";
+import { buildWorkspaceKernelItemPathIndex } from "#/features/workspaces/kernel/workspace-kernel-paths";
+
+const emptyBytes = new Uint8Array();
+const textEncoder = new TextEncoder();
+
+interface WorkspaceExportReaders {
+	readDocument: (item: WorkspaceItemSummary) => TiptapDocumentJson;
+	readFile: (item: WorkspaceItemSummary) => Promise<ReadableStream<Uint8Array>>;
+}
+
+export function createWorkspaceExportStream(
+	items: readonly WorkspaceItemSummary[],
+	readers: WorkspaceExportReaders,
+) {
+	const { readable, writable } = new TransformStream<Uint8Array, Uint8Array>();
+	void writeWorkspaceExport(writable, items, readers);
+	return readable;
+}
+
+async function writeWorkspaceExport(
+	writable: WritableStream<Uint8Array>,
+	items: readonly WorkspaceItemSummary[],
+	readers: WorkspaceExportReaders,
+) {
+	const writer = writable.getWriter();
+	let output = Promise.resolve();
+	const zip = new Zip((error, data, final) => {
+		if (error) {
+			output = output.then(() => writer.abort(error));
+			return;
+		}
+
+		output = output.then(() => writer.write(data));
+		if (final) {
+			output = output.then(() => writer.close());
+		}
+	});
+
+	try {
+		const paths = buildWorkspaceKernelItemPathIndex([...items]);
+		const archivePaths = buildArchivePathIndex(items, paths);
+		for (const item of items) {
+			const path = archivePaths.get(item.id);
+			if (!path) {
+				continue;
+			}
+
+			if (item.type === "folder") {
+				await addZipBytes(zip, `${path}/`, emptyBytes, () => output);
+				continue;
+			}
+			if (item.type === "document") {
+				const markdown = serializeTiptapDocumentToMarkdown(readers.readDocument(item));
+				await addZipBytes(zip, path, textEncoder.encode(`${markdown}\n`), () => output);
+				continue;
+			}
+			if (item.type === "file") {
+				await addZipStream(zip, path, await readers.readFile(item), () => output);
+			}
+		}
+
+		zip.end();
+		await output;
+	} catch (error) {
+		zip.terminate();
+		await writer.abort(error).catch(() => undefined);
+	}
+}
+
+function buildArchivePathIndex(
+	items: readonly WorkspaceItemSummary[],
+	workspacePaths: ReadonlyMap<string, string>,
+) {
+	const archivePaths = new Map<string, string>();
+	const reservedPaths = new Set<string>();
+
+	for (const item of items) {
+		if (item.type !== "folder" && item.type !== "file") {
+			continue;
+		}
+		const path = workspacePaths.get(item.id)?.slice(1);
+		if (path) {
+			archivePaths.set(item.id, path);
+			reservedPaths.add(path.toLowerCase());
+		}
+	}
+
+	for (const item of items) {
+		if (item.type !== "document") {
+			continue;
+		}
+		const workspacePath = workspacePaths.get(item.id)?.slice(1);
+		if (!workspacePath) {
+			continue;
+		}
+
+		const markdownPath = workspacePath.toLowerCase().endsWith(".md")
+			? workspacePath
+			: `${workspacePath}.md`;
+		const path = reserveArchivePath(markdownPath, reservedPaths);
+		archivePaths.set(item.id, path);
+		reservedPaths.add(path.toLowerCase());
+	}
+
+	return archivePaths;
+}
+
+function reserveArchivePath(path: string, reservedPaths: ReadonlySet<string>) {
+	if (!reservedPaths.has(path.toLowerCase())) {
+		return path;
+	}
+
+	const base = path.slice(0, -3);
+	for (let suffix = 2; ; suffix += 1) {
+		const candidate = `${base} (${suffix}).md`;
+		if (!reservedPaths.has(candidate.toLowerCase())) {
+			return candidate;
+		}
+	}
+}
+
+async function addZipBytes(
+	zip: Zip,
+	path: string,
+	bytes: Uint8Array,
+	getOutput: () => Promise<void>,
+) {
+	const file = new ZipPassThrough(path);
+	zip.add(file);
+	file.push(bytes, true);
+	await getOutput();
+}
+
+async function addZipStream(
+	zip: Zip,
+	path: string,
+	stream: ReadableStream<Uint8Array>,
+	getOutput: () => Promise<void>,
+) {
+	const file = new ZipPassThrough(path);
+	zip.add(file);
+	const reader = stream.getReader();
+
+	try {
+		while (true) {
+			const { done, value } = await reader.read();
+			if (done) {
+				file.push(emptyBytes, true);
+				await getOutput();
+				return;
+			}
+
+			file.push(value);
+			await getOutput();
+		}
+	} catch (error) {
+		await reader.cancel(error).catch(() => undefined);
+		throw error;
+	} finally {
+		reader.releaseLock();
+	}
+}
diff --git a/src/features/workspaces/export/workspace-export.ts b/src/features/workspaces/export/workspace-export.ts
new file mode 100644
index 000000000..4d8163196
--- /dev/null
+++ b/src/features/workspaces/export/workspace-export.ts
@@ -0,0 +1,63 @@
+import { env } from "cloudflare:workers";
+
+import { normalizeWorkspaceItemName } from "#/features/workspaces/defaults";
+import {
+	parseTiptapDocumentJson,
+	type TiptapDocumentJson,
+} from "#/features/workspaces/documents/tiptap-document";
+import { createWorkspaceExportStream } from "#/features/workspaces/export/workspace-export-archive";
+import { getWorkspaceKernel } from "#/features/workspaces/kernel/workspace-kernel-access";
+import { WorkspaceForbiddenError } from "#/features/workspaces/server/permissions";
+import { getWorkspacePageForUser } from "#/features/workspaces/server/queries";
+
+export async function createWorkspaceExport(input: { workspaceId: string; userId: string }) {
+	const page = await getWorkspacePageForUser(input.workspaceId, input.userId);
+	if (!page) {
+		throw new WorkspaceForbiddenError();
+	}
+
+	const kernel = await getWorkspaceKernel(input.workspaceId);
+	const documents = new Map<string, TiptapDocumentJson>();
+	const fileObjectKeys = new Map<string, string>();
+
+	// Resolve fallible metadata before the response starts streaming. Once ZIP
+	// bytes are sent, an error can only abort the download and leave a partial archive.
+	for (const item of page.items) {
+		if (item.type === "document") {
+			const { content } = await kernel.readDocumentCheckpoint({ itemId: item.id });
+			documents.set(item.id, parseTiptapDocumentJson(content));
+			continue;
+		}
+		if (item.type === "file") {
+			const source = await kernel.getFileSource({ itemId: item.id });
+			if (!(await env.WORKSPACE_KERNEL_FILES.head(source.objectKey))) {
+				throw new Error(`Workspace file source is missing for ${item.name}.`);
+			}
+			fileObjectKeys.set(item.id, source.objectKey);
+		}
+	}
+
+	return {
+		fileName: `${normalizeWorkspaceItemName(page.workspace.name, "Workspace")}-${new Date().toISOString().slice(0, 10)}.zip`,
+		stream: createWorkspaceExportStream(page.items, {
+			readDocument: (item) => {
+				const document = documents.get(item.id);
+				if (!document) {
+					throw new Error(`Workspace document was not prepared for ${item.name}.`);
+				}
+				return document;
+			},
+			readFile: async (item) => {
+				const objectKey = fileObjectKeys.get(item.id);
+				if (!objectKey) {
+					throw new Error(`Workspace file was not prepared for ${item.name}.`);
+				}
+				const object = await env.WORKSPACE_KERNEL_FILES.get(objectKey);
+				if (!object) {
+					throw new Error(`Workspace file source is missing for ${item.name}.`);
+				}
+				return object.body;
+			},
+		}),
+	};
+}
diff --git a/src/features/workspaces/kernel/workspace-kernel-store.ts b/src/features/workspaces/kernel/workspace-kernel-store.ts
index 018db6023..90356671b 100644
--- a/src/features/workspaces/kernel/workspace-kernel-store.ts
+++ b/src/features/workspaces/kernel/workspace-kernel-store.ts
@@ -5,6 +5,7 @@ import type {
 } from "#/features/workspaces/contracts";
 import {
 	getAvailableWorkspaceItemName,
+	getWorkspaceItemNameKey,
 	normalizeWorkspaceItemName,
 } from "#/features/workspaces/defaults";
 import {
@@ -200,11 +201,10 @@ export class WorkspaceKernelStore {
 			...this.getActiveSiblingNames(input.parentId, input.excludeItemId),
 			...(input.reservedNames ?? []),
 		];
-		const requestedName = input.requestedName
-			? normalizeWorkspaceItemName(input.requestedName, "")
-			: "";
-
 		if (input.onNameConflict === "error") {
+			const requestedName = input.requestedName
+				? normalizeWorkspaceItemName(input.requestedName, "")
+				: "";
 			if (!requestedName) {
 				return {
 					conflict: {
@@ -216,7 +216,12 @@ export class WorkspaceKernelStore {
 				};
 			}
 
-			if (existingNames.includes(requestedName)) {
+			if (
+				existingNames.some(
+					(existingName) =>
+						getWorkspaceItemNameKey(existingName) === getWorkspaceItemNameKey(requestedName),
+				)
+			) {
 				return {
 					conflict: {
 						code: "name_conflict",
diff --git a/src/features/workspaces/operations/create-items.ts b/src/features/workspaces/operations/create-items.ts
index 671b3204d..08e53b467 100644
--- a/src/features/workspaces/operations/create-items.ts
+++ b/src/features/workspaces/operations/create-items.ts
@@ -54,7 +54,7 @@ export interface CreateWorkspaceItemsOperationResult {
 
 type CreateWorkspaceItemPathResolution =
 	| {
-			code: "cannot_create_root" | "path_not_absolute" | "path_not_canonical";
+			code: "cannot_create_root" | "path_not_absolute";
 			path: string;
 			status: "failed";
 	  }
@@ -247,14 +247,6 @@ function resolveCreateWorkspaceItemPath(path: string): CreateWorkspaceItemPathRe
 		const name = getWorkspacePathName(normalizedPath);
 		const canonicalPath = joinWorkspaceItemPath(parentPath, name);
 
-		if (canonicalPath !== normalizedPath) {
-			return {
-				code: "path_not_canonical",
-				path: normalizedPath,
-				status: "failed",
-			};
-		}
-
 		return {
 			name,
 			parentPath,
diff --git a/src/features/workspaces/operations/workspace-operation-failure-codes.ts b/src/features/workspaces/operations/workspace-operation-failure-codes.ts
index 6294c9d7b..c5c54e0c1 100644
--- a/src/features/workspaces/operations/workspace-operation-failure-codes.ts
+++ b/src/features/workspaces/operations/workspace-operation-failure-codes.ts
@@ -11,7 +11,6 @@ export const createWorkspaceItemsFailureCodes = [
 	"invalid_initial_content",
 	"path_already_exists",
 	"path_not_absolute",
-	"path_not_canonical",
 	"path_not_folder",
 	"path_not_found",
 	...workspaceRelationFailureCodes,
diff --git a/src/features/workspaces/operations/workspace-tool-schemas.ts b/src/features/workspaces/operations/workspace-tool-schemas.ts
index 4d9247c92..4262cb413 100644
--- a/src/features/workspaces/operations/workspace-tool-schemas.ts
+++ b/src/features/workspaces/operations/workspace-tool-schemas.ts
@@ -13,6 +13,7 @@ import {
 	renameWorkspaceItemFailureCodes,
 } from "#/features/workspaces/operations/workspace-operation-failure-codes";
 import {
+	WORKSPACE_ITEM_NAME_MAX_LENGTH,
 	workspaceItemTypeSchema,
 	workspaceRelationKindSchema,
 } from "#/features/workspaces/contracts";
@@ -151,7 +152,12 @@ export const workspaceLinkItemsInputSchema = z.object({
 });
 
 export const workspaceRenameItemInputSchema = z.object({
-	name: z.string().trim().min(1).max(160).describe("New user-visible item name."),
+	name: z
+		.string()
+		.trim()
+		.min(1)
+		.max(WORKSPACE_ITEM_NAME_MAX_LENGTH)
+		.describe("New user-visible item name."),
 	path: z.string().min(1).describe("Absolute path of one actual ThinkEx workspace item to rename."),
 });
 
diff --git a/src/features/workspaces/server/queries.ts b/src/features/workspaces/server/queries.ts
index d0a8d4360..d8ba45849 100644
--- a/src/features/workspaces/server/queries.ts
+++ b/src/features/workspaces/server/queries.ts
@@ -51,41 +51,58 @@ export async function getWorkspacePageForCurrentUser(
 	const [userId, dbContext] = await Promise.all([getCurrentUserId(), createDbContext()]);
 
 	try {
-		const [workspaceRow] = await dbContext.db
-			.select({
-				lastOpenedAt: workspaceMembers.lastOpenedAt,
-				membershipRole: workspaceMembers.role,
-				workspace: workspaces,
-			})
-			.from(workspaceMembers)
-			.innerJoin(workspaces, eq(workspaceMembers.workspaceId, workspaces.id))
-			.where(
-				and(
-					eq(workspaceMembers.workspaceId, workspaceId),
-					eq(workspaceMembers.userId, userId),
-					isNull(workspaces.archivedAt),
-				),
-			)
-			.limit(1);
-
-		if (!workspaceRow) {
-			return null;
-		}
+		return await getWorkspacePage(dbContext.db, workspaceId, userId);
+	} finally {
+		await dbContext.dispose();
+	}
+}
 
-		const workspace = mapWorkspaceDetailRow(
-			{
-				...workspaceRow.workspace,
-				lastOpenedAt: workspaceRow.lastOpenedAt,
-			},
-			workspaceRow.membershipRole,
-		);
+export async function getWorkspacePageForUser(
+	workspaceId: string,
+	userId: string,
+): Promise<WorkspacePage | null> {
+	const dbContext = await createDbContext();
 
-		return await getWorkspaceKernelPage({
-			workspaceId,
-			userId,
-			workspace,
-		});
+	try {
+		return await getWorkspacePage(dbContext.db, workspaceId, userId);
 	} finally {
 		await dbContext.dispose();
 	}
 }
+
+async function getWorkspacePage(db: Db, workspaceId: string, userId: string) {
+	const [workspaceRow] = await db
+		.select({
+			lastOpenedAt: workspaceMembers.lastOpenedAt,
+			membershipRole: workspaceMembers.role,
+			workspace: workspaces,
+		})
+		.from(workspaceMembers)
+		.innerJoin(workspaces, eq(workspaceMembers.workspaceId, workspaces.id))
+		.where(
+			and(
+				eq(workspaceMembers.workspaceId, workspaceId),
+				eq(workspaceMembers.userId, userId),
+				isNull(workspaces.archivedAt),
+			),
+		)
+		.limit(1);
+
+	if (!workspaceRow) {
+		return null;
+	}
+
+	const workspace = mapWorkspaceDetailRow(
+		{
+			...workspaceRow.workspace,
+			lastOpenedAt: workspaceRow.lastOpenedAt,
+		},
+		workspaceRow.membershipRole,
+	);
+
+	return await getWorkspaceKernelPage({
+		workspaceId,
+		userId,
+		workspace,
+	});
+}
diff --git a/src/routeTree.gen.ts b/src/routeTree.gen.ts
index 7ff8bc377..fc83da84a 100644
--- a/src/routeTree.gen.ts
+++ b/src/routeTree.gen.ts
@@ -30,6 +30,7 @@ import { Route as ProtectedWorkspacesWorkspaceIdRouteImport } from './routes/_pr
 import { Route as ApiAuthSplatRouteImport } from './routes/api/auth/$'
 import { Route as ApiPosthogSurveyFeedbackRouteImport } from './routes/api/posthog/survey-feedback'
 import { Route as ApiV1WorkspacesRouteImport } from './routes/api/v1/workspaces'
+import { Route as ApiV1WorkspacesWorkspaceIdExportRouteImport } from './routes/api/v1/workspaces.$workspaceId.export'
 import { Route as ApiV1WorkspacesWorkspaceIdFileUploadRouteImport } from './routes/api/v1/workspaces.$workspaceId.file-upload'
 import { Route as ApiV1WorkspacesWorkspaceIdAiThreadsThreadIdAttachmentsRouteImport } from './routes/api/v1/workspaces.$workspaceId.ai-threads.$threadId.attachments'
 import { Route as ApiV1WorkspacesWorkspaceIdFilesItemIdContentRouteImport } from './routes/api/v1/workspaces.$workspaceId.files.$itemId.content'
@@ -142,6 +143,12 @@ const ApiV1WorkspacesRoute = ApiV1WorkspacesRouteImport.update({
   path: '/api/v1/workspaces',
   getParentRoute: () => rootRouteImport,
 } as any)
+const ApiV1WorkspacesWorkspaceIdExportRoute =
+  ApiV1WorkspacesWorkspaceIdExportRouteImport.update({
+    id: '/$workspaceId/export',
+    path: '/$workspaceId/export',
+    getParentRoute: () => ApiV1WorkspacesRoute,
+  } as any)
 const ApiV1WorkspacesWorkspaceIdFileUploadRoute =
   ApiV1WorkspacesWorkspaceIdFileUploadRouteImport.update({
     id: '/$workspaceId/file-upload',
@@ -197,6 +204,7 @@ export interface FileRoutesByFullPath {
   '/api/auth/$': typeof ApiAuthSplatRoute
   '/api/posthog/survey-feedback': typeof ApiPosthogSurveyFeedbackRoute
   '/api/v1/workspaces': typeof ApiV1WorkspacesRouteWithChildren
+  '/api/v1/workspaces/$workspaceId/export': typeof ApiV1WorkspacesWorkspaceIdExportRoute
   '/api/v1/workspaces/$workspaceId/file-upload': typeof ApiV1WorkspacesWorkspaceIdFileUploadRoute
   '/api/v1/workspaces/$workspaceId/ai-threads/$threadId/attachments': typeof ApiV1WorkspacesWorkspaceIdAiThreadsThreadIdAttachmentsRouteWithChildren
   '/api/v1/workspaces/$workspaceId/files/$itemId/content': typeof ApiV1WorkspacesWorkspaceIdFilesItemIdContentRoute
@@ -223,6 +231,7 @@ export interface FileRoutesByTo {
   '/api/auth/$': typeof ApiAuthSplatRoute
   '/api/posthog/survey-feedback': typeof ApiPosthogSurveyFeedbackRoute
   '/api/v1/workspaces': typeof ApiV1WorkspacesRouteWithChildren
+  '/api/v1/workspaces/$workspaceId/export': typeof ApiV1WorkspacesWorkspaceIdExportRoute
   '/api/v1/workspaces/$workspaceId/file-upload': typeof ApiV1WorkspacesWorkspaceIdFileUploadRoute
   '/api/v1/workspaces/$workspaceId/ai-threads/$threadId/attachments': typeof ApiV1WorkspacesWorkspaceIdAiThreadsThreadIdAttachmentsRouteWithChildren
   '/api/v1/workspaces/$workspaceId/files/$itemId/content': typeof ApiV1WorkspacesWorkspaceIdFilesItemIdContentRoute
@@ -252,6 +261,7 @@ export interface FileRoutesById {
   '/api/auth/$': typeof ApiAuthSplatRoute
   '/api/posthog/survey-feedback': typeof ApiPosthogSurveyFeedbackRoute
   '/api/v1/workspaces': typeof ApiV1WorkspacesRouteWithChildren
+  '/api/v1/workspaces/$workspaceId/export': typeof ApiV1WorkspacesWorkspaceIdExportRoute
   '/api/v1/workspaces/$workspaceId/file-upload': typeof ApiV1WorkspacesWorkspaceIdFileUploadRoute
   '/api/v1/workspaces/$workspaceId/ai-threads/$threadId/attachments': typeof ApiV1WorkspacesWorkspaceIdAiThreadsThreadIdAttachmentsRouteWithChildren
   '/api/v1/workspaces/$workspaceId/files/$itemId/content': typeof ApiV1WorkspacesWorkspaceIdFilesItemIdContentRoute
@@ -281,6 +291,7 @@ export interface FileRouteTypes {
     | '/api/auth/$'
     | '/api/posthog/survey-feedback'
     | '/api/v1/workspaces'
+    | '/api/v1/workspaces/$workspaceId/export'
     | '/api/v1/workspaces/$workspaceId/file-upload'
     | '/api/v1/workspaces/$workspaceId/ai-threads/$threadId/attachments'
     | '/api/v1/workspaces/$workspaceId/files/$itemId/content'
@@ -307,6 +318,7 @@ export interface FileRouteTypes {
     | '/api/auth/$'
     | '/api/posthog/survey-feedback'
     | '/api/v1/workspaces'
+    | '/api/v1/workspaces/$workspaceId/export'
     | '/api/v1/workspaces/$workspaceId/file-upload'
     | '/api/v1/workspaces/$workspaceId/ai-threads/$threadId/attachments'
     | '/api/v1/workspaces/$workspaceId/files/$itemId/content'
@@ -335,6 +347,7 @@ export interface FileRouteTypes {
     | '/api/auth/$'
     | '/api/posthog/survey-feedback'
     | '/api/v1/workspaces'
+    | '/api/v1/workspaces/$workspaceId/export'
     | '/api/v1/workspaces/$workspaceId/file-upload'
     | '/api/v1/workspaces/$workspaceId/ai-threads/$threadId/attachments'
     | '/api/v1/workspaces/$workspaceId/files/$itemId/content'
@@ -509,6 +522,13 @@ declare module '@tanstack/react-router' {
       preLoaderRoute: typeof ApiV1WorkspacesRouteImport
       parentRoute: typeof rootRouteImport
     }
+    '/api/v1/workspaces/$workspaceId/export': {
+      id: '/api/v1/workspaces/$workspaceId/export'
+      path: '/$workspaceId/export'
+      fullPath: '/api/v1/workspaces/$workspaceId/export'
+      preLoaderRoute: typeof ApiV1WorkspacesWorkspaceIdExportRouteImport
+      parentRoute: typeof ApiV1WorkspacesRoute
+    }
     '/api/v1/workspaces/$workspaceId/file-upload': {
       id: '/api/v1/workspaces/$workspaceId/file-upload'
       path: '/$workspaceId/file-upload'
@@ -593,6 +613,7 @@ const ApiV1WorkspacesWorkspaceIdAiThreadsThreadIdAttachmentsRouteWithChildren =
   )
 
 interface ApiV1WorkspacesRouteChildren {
+  ApiV1WorkspacesWorkspaceIdExportRoute: typeof ApiV1WorkspacesWorkspaceIdExportRoute
   ApiV1WorkspacesWorkspaceIdFileUploadRoute: typeof ApiV1WorkspacesWorkspaceIdFileUploadRoute
   ApiV1WorkspacesWorkspaceIdAiThreadsThreadIdAttachmentsRoute: typeof ApiV1WorkspacesWorkspaceIdAiThreadsThreadIdAttachmentsRouteWithChildren
   ApiV1WorkspacesWorkspaceIdFilesItemIdContentRoute: typeof ApiV1WorkspacesWorkspaceIdFilesItemIdContentRoute
@@ -600,6 +621,7 @@ interface ApiV1WorkspacesRouteChildren {
 }
 
 const ApiV1WorkspacesRouteChildren: ApiV1WorkspacesRouteChildren = {
+  ApiV1WorkspacesWorkspaceIdExportRoute: ApiV1WorkspacesWorkspaceIdExportRoute,
   ApiV1WorkspacesWorkspaceIdFileUploadRoute:
     ApiV1WorkspacesWorkspaceIdFileUploadRoute,
   ApiV1WorkspacesWorkspaceIdAiThreadsThreadIdAttachmentsRoute:
diff --git a/src/routes/api/v1/workspaces.$workspaceId.export.ts b/src/routes/api/v1/workspaces.$workspaceId.export.ts
new file mode 100644
index 000000000..cca1ec8fb
--- /dev/null
+++ b/src/routes/api/v1/workspaces.$workspaceId.export.ts
@@ -0,0 +1,56 @@
+import { createFileRoute } from "@tanstack/react-router";
+
+import { createWorkspaceExport } from "#/features/workspaces/export/workspace-export";
+import { WorkspaceForbiddenError } from "#/features/workspaces/server/permissions";
+import { apiError, getRequestId } from "#/lib/api/http";
+import { getSessionFromRequest } from "#/lib/auth-queries.server";
+
+async function handleWorkspaceExport(request: Request, workspaceId: string) {
+	const requestId = getRequestId(request);
+	const session = await getSessionFromRequest(request);
+	if (!session) {
+		return apiError(requestId, 401, "UNAUTHORIZED", "You must be signed in to export a workspace.");
+	}
+
+	try {
+		const archive = await createWorkspaceExport({
+			workspaceId,
+			userId: session.user.id,
+		});
+		return new Response(archive.stream, {
+			headers: {
+				"cache-control": "private, no-store",
+				"content-disposition": getAttachmentHeader(archive.fileName),
+				"content-type": "application/zip",
+				"x-request-id": requestId,
+			},
+		});
+	} catch (error) {
+		if (error instanceof WorkspaceForbiddenError) {
+			return apiError(
+				requestId,
+				403,
+				"FORBIDDEN",
+				"You do not have permission to export this workspace.",
+			);
+		}
+
+		console.error("Workspace export failed.", { error, requestId, workspaceId });
+		return apiError(requestId, 500, "EXPORT_FAILED", "Unable to export this workspace.");
+	}
+}
+
+export const Route = createFileRoute("/api/v1/workspaces/$workspaceId/export")({
+	server: {
+		handlers: {
+			GET: ({ params, request }) => handleWorkspaceExport(request, params.workspaceId),
+		},
+	},
+});
+
+function getAttachmentHeader(fileName: string) {
+	const fallback = fileName.replace(/[^\x20-\x7e]|["\\]/g, "_");
+	return `attachment; filename="${fallback}"; filename*=UTF-8''${encodeURIComponent(fileName)}`;
+}
+
+export { handleWorkspaceExport };