diff --git a/packages/core/src/orchestrator/orchestrator-agent.test.ts b/packages/core/src/orchestrator/orchestrator-agent.test.ts
index ab8165ca7e..ed9fc9ef4a 100644
--- a/packages/core/src/orchestrator/orchestrator-agent.test.ts
+++ b/packages/core/src/orchestrator/orchestrator-agent.test.ts
@@ -902,10 +902,12 @@ describe('discoverAllWorkflows — remote sync', () => {
     mockSendQuery.mockClear();
     mockGetCodebaseEnvVars.mockReset();
     mockLoadConfig.mockReset();
+    mockListCodebases.mockReset();
     // Reset mocks between tests in this suite and restore safe defaults
     mockGetOrCreateConversation.mockImplementation(() => Promise.resolve(null));
     mockGetCodebase.mockImplementation(() => Promise.resolve(null));
     mockGetCodebaseEnvVars.mockImplementation(() => Promise.resolve({}));
+    mockListCodebases.mockImplementation(() => Promise.resolve([]));
     mockLoadConfig.mockImplementation(() =>
       Promise.resolve({
         assistants: { claude: {}, codex: {} },
@@ -1043,6 +1045,61 @@ describe('discoverAllWorkflows — remote sync', () => {
     const requestOptions = mockSendQuery.mock.calls[0][3] as Record<string, unknown>;
     expect(requestOptions.env).toEqual({ FILE_SECRET: 'file-value' });
   });
+
+  describe('provider cwd resolution', () => {
+    function getCwdPassedToProvider(): string {
+      expect(mockSendQuery).toHaveBeenCalled();
+      return mockSendQuery.mock.calls[0][1] as string;
+    }
+
+    test('passes codebase.default_cwd to provider when conversation is codebase-scoped', async () => {
+      const codebase = makeCodebaseForSync();
+      const conversation = makeConversation({ codebase_id: 'codebase-1', cwd: null });
+      mockGetOrCreateConversation.mockReturnValueOnce(Promise.resolve(conversation));
+      mockGetCodebase.mockReturnValueOnce(Promise.resolve(codebase));
+      mockListCodebases.mockReturnValueOnce(Promise.resolve([codebase]));
+
+      await handleMessage(makePlatform(), 'conv-1', 'What files are in src/?');
+
+      expect(getCwdPassedToProvider()).toBe('/repos/test-repo');
+    });
+
+    test('prefers conversation.cwd over codebase.default_cwd when set (worktree)', async () => {
+      const codebase = makeCodebaseForSync();
+      const conversation = makeConversation({
+        codebase_id: 'codebase-1',
+        cwd: '/home/test/.archon/workspaces/owner/repo/worktrees/feature-branch',
+      });
+      mockGetOrCreateConversation.mockReturnValueOnce(Promise.resolve(conversation));
+      mockGetCodebase.mockReturnValueOnce(Promise.resolve(codebase));
+      mockListCodebases.mockReturnValueOnce(Promise.resolve([codebase]));
+
+      await handleMessage(makePlatform(), 'conv-1', 'What files are in src/?');
+
+      expect(getCwdPassedToProvider()).toBe(
+        '/home/test/.archon/workspaces/owner/repo/worktrees/feature-branch'
+      );
+    });
+
+    test('falls back to getArchonWorkspacesPath when conversation has no codebase', async () => {
+      const conversation = makeConversation({ codebase_id: null, cwd: null });
+      mockGetOrCreateConversation.mockReturnValueOnce(Promise.resolve(conversation));
+
+      await handleMessage(makePlatform(), 'conv-1', 'Hello');
+
+      expect(getCwdPassedToProvider()).toBe('/home/test/.archon/workspaces');
+    });
+
+    test('falls back to getArchonWorkspacesPath when codebase_id is set but codebase not in list', async () => {
+      const conversation = makeConversation({ codebase_id: 'codebase-1', cwd: null });
+      mockGetOrCreateConversation.mockReturnValueOnce(Promise.resolve(conversation));
+      mockListCodebases.mockReturnValueOnce(Promise.resolve([]));
+
+      await handleMessage(makePlatform(), 'conv-1', 'Hello');
+
+      expect(getCwdPassedToProvider()).toBe('/home/test/.archon/workspaces');
+    });
+  });
 });
 
 // ─── Workflow dispatch routing — interactive flag ─────────────────────────────
diff --git a/packages/core/src/orchestrator/orchestrator-agent.ts b/packages/core/src/orchestrator/orchestrator-agent.ts
index ba24331b69..9f1b6dd558 100644
--- a/packages/core/src/orchestrator/orchestrator-agent.ts
+++ b/packages/core/src/orchestrator/orchestrator-agent.ts
@@ -809,7 +809,22 @@ export async function handleMessage(
       attachedFiles,
       workflowContext
     );
-    const cwd = getArchonWorkspacesPath();
+    // For codebase-scoped chat, use the worktree path (conversation.cwd) if set,
+    // otherwise the codebase's default working directory.
+    // Non-scoped chat falls back to the Archon workspaces root.
+    let cwd = getArchonWorkspacesPath();
+    if (conversation.codebase_id) {
+      const attachedCodebase = codebases.find(c => c.id === conversation.codebase_id);
+      if (attachedCodebase) {
+        cwd = conversation.cwd ?? attachedCodebase.default_cwd;
+      } else {
+        // Intentional fallback: codebase may have been deleted; run with workspaces root.
+        getLog().warn(
+          { codebaseId: conversation.codebase_id, conversationId },
+          'orchestrator.codebase_not_found_cwd_fallback'
+        );
+      }
+    }
 
     // 4. Update activity and get/create session
     await db.touchConversation(conversation.id);
diff --git a/packages/core/src/services/cleanup-service.test.ts b/packages/core/src/services/cleanup-service.test.ts
index 308a13c80d..000ef8757f 100644
--- a/packages/core/src/services/cleanup-service.test.ts
+++ b/packages/core/src/services/cleanup-service.test.ts
@@ -678,7 +678,7 @@ describe('runScheduledCleanup', () => {
     expect(report.removed).toHaveLength(0);
   });
 
-  test('continues processing after error on one environment', async () => {
+  test('processes all environments in batch (both paths missing)', async () => {
     mockListAllActiveWithCodebase.mockResolvedValueOnce([
       {
         id: 'env-error',