fix: pass remote OS to Toolbox agent deployment

CHANGELOG.md

@@ -8,6 +8,10 @@
   writing to `~/.ssh/config`
 - the header command falls back to the `CODER_HEADER_COMMAND` environment variable when the setting is blank, matching the Coder CLI and the VS Code extension
 
+### Fixed
+
+- pass the workspace agent's operating system to Toolbox before it deploys the remote agent
+
 ## 0.9.3 - 2026-08-11
 
 ### Changed
@@ -21,8 +25,8 @@
 
 - keep workspace polling alive when SSH config updates fail
 - improved validation and handling of workspace connection data
-- expand `~` and `$HOME` in the SSH log directory and network info directory settings, consistent with how the data
-  and binary directories are already resolved
+- expand `~` and `$HOME` in the SSH log directory and network info directory settings, consistent with how the data and
+  binary directories are already resolved
 
 ### Changed
 
@@ -58,8 +62,8 @@
 - skip the Coder TLS alternate hostname when fetching IDE metadata from JetBrains
 - notifications are now persistent popups instead of snackbars, so they survive a hidden window and no longer get
   dropped
-- workspace lists now default to `My workspaces`, so users initially see only workspaces they own. Users can
-  switch to `All workspaces`, and that selection is persisted per Coder deployment hostname.
+- workspace lists now default to `My workspaces`, so users initially see only workspaces they own. Users can switch to
+  `All workspaces`, and that selection is persisted per Coder deployment hostname.
 
 ## 0.9.0 - 2026-05-14
 
@@ -282,8 +286,8 @@
 
 ### Changed
 
-- the plugin will now remember the SSH connection state for each workspace, and it will try to automatically
-  establish it after an expired token was refreshed.
+- the plugin will now remember the SSH connection state for each workspace, and it will try to automatically establish
+  it after an expired token was refreshed.
 
 ### Fixed
 

gradle.properties

@@ -1,3 +1,3 @@
-version=0.9.3
+version=0.9.4
 group=com.coder.toolbox
 name=coder-toolbox

src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt

@@ -22,10 +22,7 @@ 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
@@ -52,11 +49,11 @@ 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
+private fun OS?.displayName(): String = when (this) {
+    OS.LINUX -> "Linux"
+    OS.WINDOWS -> "Windows"
+    OS.MAC -> "macOS"
+    null -> "unknown-OS"
 }
 
 /**
@@ -71,8 +68,7 @@ class CoderRemoteEnvironment(
     private val workspaceRefreshTrigger: Channel<Boolean>,
     private var workspace: Workspace,
     private var agent: WorkspaceAgent?,
-) : RemoteProviderEnvironment(environmentId(workspace, agent)), BeforeConnectionHook, AfterDisconnectHook,
-    WithDeploymentSettings {
+) : RemoteProviderEnvironment(environmentId(workspace, agent)), BeforeConnectionHook, AfterDisconnectHook {
     private var environmentStatus = WorkspaceAndAgentStatus.from(workspace, agent)
 
     override var name: String = environmentId(workspace, agent)
@@ -86,13 +82,6 @@ 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
@@ -236,7 +225,9 @@ class CoderRemoteEnvironment(
         if (agent == null) {
             return
         }
-        context.logger.info("Connecting to $id...")
+        context.logger.info(
+            "Launching SSH connection to $id on a ${agent?.operatingSystem.displayName()} machine"
+        )
         isConnected.update { true }
         context.settingsStore.updateAutoConnect(this.id, true)
         pollJob = pollNetworkMetrics()
@@ -378,7 +369,6 @@ class CoderRemoteEnvironment(
             connectionRequest.update {
                 true
             }
-            context.logger.info("Workspace status is ready and there is no existing connection, resuming SSH connection to $id")
         }
     }
 

src/main/kotlin/com/coder/toolbox/views/EnvironmentView.kt

@@ -5,11 +5,21 @@ import com.coder.toolbox.cli.CoderCLIManager
 import com.coder.toolbox.cli.WorkspaceAddress
 import com.coder.toolbox.sdk.v2.models.Workspace
 import com.coder.toolbox.sdk.v2.models.WorkspaceAgent
+import com.coder.toolbox.util.OS
+import com.jetbrains.toolbox.api.remoteDev.deploy.DeploymentSettings
+import com.jetbrains.toolbox.api.remoteDev.deploy.DeploymentTarget
 import com.jetbrains.toolbox.api.remoteDev.environments.SshEnvironmentContentsView
 import com.jetbrains.toolbox.api.remoteDev.ssh.SshConnectionInfo
 import java.net.URL
 import kotlin.time.Duration.Companion.seconds
 
+private fun OS?.toDeploymentTarget(): DeploymentTarget = when (this) {
+    OS.LINUX -> DeploymentTarget.LINUX
+    OS.MAC -> DeploymentTarget.MACOS
+    OS.WINDOWS -> DeploymentTarget.WINDOWS
+    else -> DeploymentTarget.AUTO
+}
+
 /**
  * A view for a single environment.  It displays the projects and IDEs.
  *
@@ -25,6 +35,14 @@ class EnvironmentView(
     private val workspace: Workspace,
     private val agent: WorkspaceAgent,
 ) : SshEnvironmentContentsView {
+
+    /**
+     * Derives the deployment target from the agent's reported OS, falling back to
+     * AUTO (automatic remote OS detection) when its OS is unknown.
+     */
+    override val deploymentSettings: DeploymentSettings
+        get() = DeploymentSettings.Default.copy(deploymentTarget = agent.operatingSystem.toDeploymentTarget())
+
     override suspend fun getConnectionInfo(): SshConnectionInfo =
         WorkspaceSshConnectionInfo(context, url, cli, workspace, agent)
 }

src/test/kotlin/com/coder/toolbox/views/EnvironmentViewTest.kt

@@ -6,6 +6,8 @@ import com.coder.toolbox.cli.WorkspaceAddress
 import com.coder.toolbox.sdk.v2.models.Workspace
 import com.coder.toolbox.sdk.v2.models.WorkspaceAgent
 import com.coder.toolbox.store.CoderSettingsStore
+import com.coder.toolbox.util.OS
+import com.jetbrains.toolbox.api.remoteDev.deploy.DeploymentTarget
 import io.mockk.every
 import io.mockk.mockk
 import kotlinx.coroutines.runBlocking
@@ -14,6 +16,30 @@ import kotlin.test.Test
 import kotlin.test.assertEquals
 
 class EnvironmentViewTest {
+    @Test
+    fun `deployment target follows the workspace agent operating system`() {
+        val context = mockk<CoderToolboxContext>(relaxed = true)
+        val cli = mockk<CoderCLIManager>()
+        val workspace = mockk<Workspace>()
+        val url = URL("https://coder.example.com")
+        val cases = listOf(
+            OS.LINUX to DeploymentTarget.LINUX,
+            OS.MAC to DeploymentTarget.MACOS,
+            OS.WINDOWS to DeploymentTarget.WINDOWS,
+            null to DeploymentTarget.AUTO,
+        )
+
+        cases.forEach { (operatingSystem, expectedTarget) ->
+            val agent = mockk<WorkspaceAgent> {
+                every { this@mockk.operatingSystem } returns operatingSystem
+            }
+
+            val deploymentSettings = EnvironmentView(context, url, cli, workspace, agent).deploymentSettings
+
+            assertEquals(expectedTarget, deploymentSettings.deploymentTarget)
+        }
+    }
+
     @Test
     fun `connection info passes the configured SSH config path to Toolbox`() = runBlocking {
         val context = mockk<CoderToolboxContext>(relaxed = true)