From b8ccd543c4ab5bae437254d7d07810c9a46f72be Mon Sep 17 00:00:00 2001
From: Matt Cowger <mcowger@users.noreply.github.com>
Date: Mon, 1 Jun 2026 00:34:51 -0700
Subject: [PATCH] fix: archive worktrees even when teardown fails

* Archive workspace record even if teardown fails

* Fix teardown test for cross-platform commands
---
 .../server/paseo-worktree-archive-service.ts  | 41 ++++++++++----
 .../src/server/worktree-session.test.ts       | 54 ++++++++++++++-----
 2 files changed, 73 insertions(+), 22 deletions(-)

diff --git a/packages/server/src/server/paseo-worktree-archive-service.ts b/packages/server/src/server/paseo-worktree-archive-service.ts
index b3d4daf55..7f271e0e0 100644
--- a/packages/server/src/server/paseo-worktree-archive-service.ts
+++ b/packages/server/src/server/paseo-worktree-archive-service.ts
@@ -5,7 +5,11 @@ import type { AgentStorage, StoredAgentRecord } from "./agent/agent-storage.js";
 import type { WorkspaceGitService } from "./workspace-git-service.js";
 import { normalizeWorkspaceId as normalizePersistedWorkspaceId } from "./workspace-registry-model.js";
 import type { GitHubService } from "../services/github-service.js";
-import { deletePaseoWorktree, resolvePaseoWorktreeRootForCwd } from "../utils/worktree.js";
+import {
+  deletePaseoWorktree,
+  resolvePaseoWorktreeRootForCwd,
+  WorktreeTeardownError,
+} from "../utils/worktree.js";
 import type { TerminalManager } from "../terminal/terminal-manager.js";
 
 export interface ArchivePaseoWorktreeDependencies {
@@ -104,14 +108,27 @@ export async function archivePaseoWorktree(
       }
     }
 
-    await deletePaseoWorktree({
-      cwd: options.repoRoot,
-      worktreePath: targetPath,
-      worktreesRoot: options.worktreesRoot,
-      paseoHome: dependencies.paseoHome,
-    });
+    let teardownError: WorktreeTeardownError | null = null;
+    try {
+      await deletePaseoWorktree({
+        cwd: options.repoRoot,
+        worktreePath: targetPath,
+        worktreesRoot: options.worktreesRoot,
+        paseoHome: dependencies.paseoHome,
+      });
+    } catch (error) {
+      if (error instanceof WorktreeTeardownError) {
+        teardownError = error;
+        dependencies.sessionLogger?.warn(
+          { err: error, targetPath },
+          "Worktree teardown failed during archive; archiving workspace record anyway",
+        );
+      } else {
+        throw error;
+      }
+    }
 
-    if (options.repoRoot) {
+    if (!teardownError && options.repoRoot) {
       try {
         await dependencies.workspaceGitService.getSnapshot(options.repoRoot, {
           force: true,
@@ -136,11 +153,17 @@ export async function archivePaseoWorktree(
         } catch (error) {
           dependencies.sessionLogger?.warn(
             { err: error, workspaceId },
-            "Failed to archive workspace record; worktree FS already removed",
+            teardownError
+              ? "Failed to archive workspace record after teardown failed"
+              : "Failed to archive workspace record; worktree FS already removed",
           );
         }
       }),
     );
+
+    if (teardownError) {
+      throw teardownError;
+    }
   } finally {
     dependencies.clearWorkspaceArchiving(affectedWorkspaceIdList);
     await dependencies.emitWorkspaceUpdatesForWorkspaceIds(affectedWorkspaceIdList);
diff --git a/packages/server/src/server/worktree-session.test.ts b/packages/server/src/server/worktree-session.test.ts
index 3a099d45c..04f7c2592 100644
--- a/packages/server/src/server/worktree-session.test.ts
+++ b/packages/server/src/server/worktree-session.test.ts
@@ -1935,8 +1935,20 @@ describe("archivePaseoWorktree", () => {
     });
   });
 
-  test("clears archiving state and leaves workspace records active when worktree delete fails", async () => {
-    const { tempDir, repoDir } = createGitRepo();
+  test("archives the workspace record even when the teardown script fails", async () => {
+    const teardownLogPath = isPlatform("win32")
+      ? 'Set-Content -Path (Join-Path $env:PASEO_SOURCE_CHECKOUT_PATH "teardown-start.log") -Value "started"'
+      : 'echo "started" > "$PASEO_SOURCE_CHECKOUT_PATH/teardown-start.log"';
+    const failingTeardownCommand = isPlatform("win32")
+      ? 'Write-Error "boom"; exit 9'
+      : "echo boom 1>&2; exit 9";
+    const { tempDir, repoDir } = createGitRepo({
+      paseoConfig: {
+        worktree: {
+          teardown: [teardownLogPath, failingTeardownCommand],
+        },
+      },
+    });
     cleanupPaths.push(tempDir);
 
     const paseoHome = path.join(tempDir, ".paseo");
@@ -1949,12 +1961,21 @@ describe("archivePaseoWorktree", () => {
       paseoHome,
     });
     const archivingByWorkspaceId = new Map<string, string>();
-    const emittedUpdates: Array<{
-      kind: "upsert";
-      workspaceId: string;
-      archivingAt: string | null;
-    }> = [];
-    const archiveWorkspaceRecord = vi.fn(async () => {});
+    const archivedWorkspaceIds = new Set<string>();
+    const emittedUpdates: Array<
+      | {
+          kind: "upsert";
+          workspaceId: string;
+          archivingAt: string | null;
+        }
+      | {
+          kind: "remove";
+          workspaceId: string;
+        }
+    > = [];
+    const archiveWorkspaceRecord = vi.fn(async (workspaceId: string) => {
+      archivedWorkspaceIds.add(workspaceId);
+    });
 
     await expect(
       archivePaseoWorktree(
@@ -1973,6 +1994,13 @@ describe("archivePaseoWorktree", () => {
           archiveWorkspaceRecord,
           emitWorkspaceUpdatesForWorkspaceIds: vi.fn(async (workspaceIds: Iterable<string>) => {
             for (const workspaceId of workspaceIds) {
+              if (archivedWorkspaceIds.has(workspaceId)) {
+                emittedUpdates.push({
+                  kind: "remove",
+                  workspaceId,
+                });
+                continue;
+              }
               emittedUpdates.push({
                 kind: "upsert",
                 workspaceId,
@@ -1996,23 +2024,23 @@ describe("archivePaseoWorktree", () => {
         },
         {
           targetPath: created.worktreePath,
-          repoRoot: null,
+          repoRoot: repoDir,
           requestId: "req-archive-delete-fails",
         },
       ),
-    ).rejects.toThrow("cwd or worktreesRoot is required to delete a Paseo worktree");
+    ).rejects.toThrow("Worktree teardown command failed");
 
     expect(existsSync(created.worktreePath)).toBe(true);
-    expect(archiveWorkspaceRecord).not.toHaveBeenCalled();
+    expect(existsSync(path.join(repoDir, "teardown-start.log"))).toBe(true);
+    expect(archiveWorkspaceRecord).toHaveBeenCalledWith(created.worktreePath);
     expect(emittedUpdates[0]).toEqual({
       kind: "upsert",
       workspaceId: created.worktreePath,
       archivingAt: expect.any(String),
     });
     expect(emittedUpdates.at(-1)).toEqual({
-      kind: "upsert",
+      kind: "remove",
       workspaceId: created.worktreePath,
-      archivingAt: null,
     });
   });