diff --git a/CHANGELOG.md b/CHANGELOG.md
index 6f0ebd8..be18a09 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,11 @@
 
 ## Unreleased
 
+### Changed
+
+- deployment target OS is now derived from the workspace agent's reported OS, falling back to automatic detection when
+  unknown
+
 ## 0.9.2 - 2026-08-06
 
 ### Fixed
diff --git a/gradle.properties b/gradle.properties
index fc64a1a..32d4626 100644
--- a/gradle.properties
+++ b/gradle.properties
@@ -1,3 +1,3 @@
-version=0.9.2
+version=0.9.3
 group=com.coder.toolbox
 name=coder-toolbox
\ No newline at end of file
diff --git a/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt b/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
index 7de4261..2810535 100644
--- a/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
+++ b/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
@@ -10,6 +10,7 @@ import com.coder.toolbox.sdk.ex.APIResponseException
 import com.coder.toolbox.sdk.v2.models.NetworkMetrics
 import com.coder.toolbox.sdk.v2.models.Workspace
 import com.coder.toolbox.sdk.v2.models.WorkspaceAgent
+import com.coder.toolbox.util.OS
 import com.coder.toolbox.util.waitForFalseWithTimeout
 import com.coder.toolbox.util.withPath
 import com.coder.toolbox.views.Action
@@ -21,7 +22,10 @@ import com.jetbrains.toolbox.api.remoteDev.AfterDisconnectHook
 import com.jetbrains.toolbox.api.remoteDev.BeforeConnectionHook
 import com.jetbrains.toolbox.api.remoteDev.EnvironmentVisibilityState
 import com.jetbrains.toolbox.api.remoteDev.RemoteProviderEnvironment
+import com.jetbrains.toolbox.api.remoteDev.deploy.DeploymentSettings
+import com.jetbrains.toolbox.api.remoteDev.deploy.DeploymentTarget
 import com.jetbrains.toolbox.api.remoteDev.environments.EnvironmentContentsView
+import com.jetbrains.toolbox.api.remoteDev.environments.WithDeploymentSettings
 import com.jetbrains.toolbox.api.remoteDev.states.EnvironmentDescription
 import com.jetbrains.toolbox.api.remoteDev.states.RemoteEnvironmentState
 import com.jetbrains.toolbox.api.ui.actions.ActionDescription
@@ -48,6 +52,13 @@ private val POLL_INTERVAL = 5.seconds
 private fun environmentId(workspace: Workspace, agent: WorkspaceAgent?): String =
     agent?.let { "${workspace.name}.${it.name}" } ?: workspace.name
 
+private fun OS?.toDeploymentTarget(): DeploymentTarget = when (this) {
+    OS.LINUX -> DeploymentTarget.LINUX
+    OS.MAC -> DeploymentTarget.MACOS
+    OS.WINDOWS -> DeploymentTarget.WINDOWS
+    else -> DeploymentTarget.AUTO
+}
+
 /**
  * Represents a workspace, or a workspace and agent combination when an agent is available.
  *
@@ -60,7 +71,8 @@ class CoderRemoteEnvironment(
     private val workspaceRefreshTrigger: Channel<Boolean>,
     private var workspace: Workspace,
     private var agent: WorkspaceAgent?,
-) : RemoteProviderEnvironment(environmentId(workspace, agent)), BeforeConnectionHook, AfterDisconnectHook {
+) : RemoteProviderEnvironment(environmentId(workspace, agent)), BeforeConnectionHook, AfterDisconnectHook,
+    WithDeploymentSettings {
     private var environmentStatus = WorkspaceAndAgentStatus.from(workspace, agent)
 
     override var name: String = environmentId(workspace, agent)
@@ -74,6 +86,13 @@ class CoderRemoteEnvironment(
     override val additionalEnvironmentInformation: MutableMap<LocalizableString, String> = mutableMapOf()
     override val actionsList: MutableStateFlow<List<ActionDescription>> = MutableStateFlow(emptyList())
 
+    /**
+     * Derives the deployment target from the agent's reported OS, falling back to
+     * AUTO (automatic remote OS detection) when the agent or its OS is unknown.
+     */
+    override val deploymentSettings: DeploymentSettings
+        get() = DeploymentSettings.Default.copy(deploymentTarget = agent?.operatingSystem.toDeploymentTarget())
+
     private val networkMetricsMarshaller = Moshi.Builder().build().adapter(NetworkMetrics::class.java)
     private val proxyCommandHandle = SshCommandProcessHandle(context)
     private var pollJob: Job? = null