diff --git a/packages/core/src/workspace.ts b/packages/core/src/workspace.ts
index 505c96231a..42cd02e091 100644
--- a/packages/core/src/workspace.ts
+++ b/packages/core/src/workspace.ts
@@ -4,6 +4,7 @@ import { Workspace } from "@opencode-ai/schema/workspace"
 import { makeGlobalNode } from "@opencode-ai/util/effect/app-node"
 import { eq } from "drizzle-orm"
 import { Clock, Context, Duration, Effect, Exit, Layer, Ref, Schedule, Schema, Scope } from "effect"
+import { systemError } from "effect/PlatformError"
 import { make as makeSpawner } from "effect/unstable/process/ChildProcessSpawner"
 import type { Driver as EnvironmentDriver } from "./environment/driver"
 import { Database } from "./database/database"
@@ -169,7 +170,17 @@ const layer = (options: Options) =>
             Effect.acquireRelease(
               locks.withLock(workspaceID)(
                 Effect.gen(function* () {
-                  const connection = yield* open(workspaceID).pipe(Effect.orDie)
+                  const connection = yield* open(workspaceID).pipe(
+                    Effect.mapError((cause) =>
+                      systemError({
+                        _tag: "Unknown",
+                        module: "Workspace",
+                        method: "spawn",
+                        description: `Failed to wake workspace ${workspaceID}`,
+                        cause,
+                      }),
+                    ),
+                  )
                   yield* Ref.set(connection.lastActivity, yield* Clock.currentTimeMillis)
                   yield* Ref.update(connection.active, (active) => active + 1)
                   return connection
@@ -184,6 +195,7 @@ const layer = (options: Options) =>
                 ),
             ).pipe(Effect.flatMap((connection) => connection.environment.spawner.spawn(command))),
           )
+          // Overrides are connection-bound; route them per spawn before any workspace driver ships them.
           return { spawner, overrides: initial.environment.overrides }
         }),
         destroy: Effect.fn("Workspace.destroy")(function* (workspaceID) {
diff --git a/packages/core/test/workspace.test.ts b/packages/core/test/workspace.test.ts
index e39ad33b09..78ec2666bc 100644
--- a/packages/core/test/workspace.test.ts
+++ b/packages/core/test/workspace.test.ts
@@ -15,6 +15,7 @@ import { testEffect } from "./lib/effect"
 
 const calls: Array<{ readonly operation: string; readonly binding?: WorkspaceDriver.Binding }> = []
 const memory = makeMemoryDriver()
+let failConnect = false
 
 const driver = WorkspaceDriver.make({
   create: ({ workspaceID }) => {
@@ -23,6 +24,7 @@ const driver = WorkspaceDriver.make({
   },
   connect: ({ binding }) => {
     calls.push({ operation: "connect", binding })
+    if (failConnect) return Effect.fail(new WorkspaceDriver.Error({ message: "wake failed" }))
     return Effect.succeed(memory)
   },
   suspendForIdle: ({ binding, saveBinding }) => {
@@ -51,7 +53,10 @@ const it = testEffect(
   ),
 )
 
-beforeEach(() => calls.splice(0))
+beforeEach(() => {
+  calls.splice(0)
+  failConnect = false
+})
 
 it.effect("persists the workspace lifecycle and reconnects after idle suspension", () =>
   Effect.gen(function* () {
@@ -97,3 +102,25 @@ it.effect("roundtrips nullable bindings through the workspace table", () =>
     expect(row).toEqual({ id, provider: "fake", binding: null, created_at: 10, last_used_at: 20 })
   }),
 )
+
+it.effect("surfaces wake failures through the spawn error channel", () =>
+  Effect.gen(function* () {
+    const workspace = yield* Workspace.Service
+    const created = yield* workspace.create("fake")
+    const environment = yield* workspace.connect(created.id)
+
+    yield* TestClock.adjust("6 minutes")
+    failConnect = true
+
+    const error = yield* Effect.scoped(environment.spawner.spawn(ChildProcess.make("wake"))).pipe(Effect.flip)
+    expect(error).toMatchObject({
+      _tag: "PlatformError",
+      reason: {
+        _tag: "Unknown",
+        module: "Workspace",
+        method: "spawn",
+        description: `Failed to wake workspace ${created.id}`,
+      },
+    })
+  }),
+)