From 0cb6387a689b7e221de41e1149cf8593f12adfb9 Mon Sep 17 00:00:00 2001
From: Julius Marminge <julius0216@outlook.com>
Date: Sat, 20 Jun 2026 18:43:36 -0700
Subject: [PATCH] Structure workspace search cleanup failures

Co-authored-by: codex <codex@users.noreply.github.com>
---
 apps/server/src/workspace/WorkspaceEntries.ts | 27 ++++++++++------
 .../workspace/WorkspaceSearchIndex.test.ts    | 31 +++++++++++++++++++
 .../src/workspace/WorkspaceSearchIndex.ts     | 17 +++++++++-
 3 files changed, 65 insertions(+), 10 deletions(-)

diff --git a/apps/server/src/workspace/WorkspaceEntries.ts b/apps/server/src/workspace/WorkspaceEntries.ts
index 81fb735ea2e..7501cbe0eab 100644
--- a/apps/server/src/workspace/WorkspaceEntries.ts
+++ b/apps/server/src/workspace/WorkspaceEntries.ts
@@ -151,20 +151,29 @@ export const make = Effect.gen(function* () {
       if (!(yield* RcMap.has(workspaceSearchIndexes.rcMap, normalizedCwd))) {
         return;
       }
+      const recoverRefreshFailure = (
+        cause:
+          | WorkspaceSearchIndex.WorkspaceSearchIndexCreateFailed
+          | WorkspaceSearchIndex.WorkspaceSearchIndexScanTimedOut
+          | WorkspaceSearchIndex.WorkspaceSearchIndexRefreshFailed,
+      ) =>
+        Effect.gen(function* () {
+          yield* Effect.logWarning("Failed to refresh workspace search index", {
+            cwd,
+            cause,
+          });
+          yield* workspaceSearchIndexes.invalidate(normalizedCwd);
+        });
       yield* Effect.gen(function* () {
         const searchIndex = yield* WorkspaceSearchIndex.WorkspaceSearchIndex;
         yield* searchIndex.refresh();
       }).pipe(
         Effect.provide(workspaceSearchIndexes.get(normalizedCwd)),
-        Effect.catch((cause) =>
-          Effect.gen(function* () {
-            yield* Effect.logWarning("Failed to refresh workspace search index", {
-              cwd,
-              cause,
-            });
-            yield* workspaceSearchIndexes.invalidate(normalizedCwd);
-          }),
-        ),
+        Effect.catchTags({
+          WorkspaceSearchIndexCreateFailed: recoverRefreshFailure,
+          WorkspaceSearchIndexScanTimedOut: recoverRefreshFailure,
+          WorkspaceSearchIndexRefreshFailed: recoverRefreshFailure,
+        }),
       );
     },
   );
diff --git a/apps/server/src/workspace/WorkspaceSearchIndex.test.ts b/apps/server/src/workspace/WorkspaceSearchIndex.test.ts
index 41ea90b9735..9b7ed4e2453 100644
--- a/apps/server/src/workspace/WorkspaceSearchIndex.test.ts
+++ b/apps/server/src/workspace/WorkspaceSearchIndex.test.ts
@@ -1,6 +1,8 @@
 import { FileFinder } from "@ff-labs/fff-node";
 import { afterEach, expect, it } from "@effect/vitest";
+import * as Cause from "effect/Cause";
 import * as Effect from "effect/Effect";
+import * as Exit from "effect/Exit";
 import { vi } from "vite-plus/test";
 
 import * as WorkspaceSearchIndex from "./WorkspaceSearchIndex.ts";
@@ -49,6 +51,35 @@ it.effect("keeps returned FileFinder creation diagnostics out of the cause chain
   }),
 );
 
+it.effect("preserves FileFinder destroy failures as structured defects", () =>
+  Effect.gen(function* () {
+    const cause = new Error("native destroy failed");
+    const finder = {
+      destroy: vi.fn(() => {
+        throw cause;
+      }),
+      isScanning: vi.fn(() => false),
+    } as unknown as FileFinder;
+    vi.spyOn(FileFinder, "create").mockReturnValueOnce({ ok: true, value: finder });
+
+    const exit = yield* Effect.scoped(WorkspaceSearchIndex.make("/workspace/project")).pipe(
+      Effect.exit,
+    );
+
+    expect(Exit.isFailure(exit)).toBe(true);
+    if (Exit.isFailure(exit)) {
+      expect(Cause.hasDies(exit.cause)).toBe(true);
+      const error = Cause.squash(exit.cause);
+      expect(error).toBeInstanceOf(WorkspaceSearchIndex.WorkspaceSearchIndexDestroyFailed);
+      expect(error).toMatchObject({
+        _tag: "WorkspaceSearchIndexDestroyFailed",
+        cwd: "/workspace/project",
+        cause,
+      });
+    }
+  }),
+);
+
 it.effect("preserves search and refresh failures with operation context", () =>
   Effect.scoped(
     Effect.gen(function* () {
diff --git a/apps/server/src/workspace/WorkspaceSearchIndex.ts b/apps/server/src/workspace/WorkspaceSearchIndex.ts
index 2b043e05c0e..db4d46851e7 100644
--- a/apps/server/src/workspace/WorkspaceSearchIndex.ts
+++ b/apps/server/src/workspace/WorkspaceSearchIndex.ts
@@ -71,6 +71,18 @@ export class WorkspaceSearchIndexRefreshFailed extends Schema.TaggedErrorClass<W
   }
 }
 
+export class WorkspaceSearchIndexDestroyFailed extends Schema.TaggedErrorClass<WorkspaceSearchIndexDestroyFailed>()(
+  "WorkspaceSearchIndexDestroyFailed",
+  {
+    cwd: Schema.String,
+    cause: Schema.Defect(),
+  },
+) {
+  override get message(): string {
+    return `Failed to destroy the workspace search index for '${this.cwd}'.`;
+  }
+}
+
 export type WorkspaceSearchIndexError =
   | WorkspaceSearchIndexCreateFailed
   | WorkspaceSearchIndexScanTimedOut
@@ -201,7 +213,10 @@ const waitForScan = <E>(cwd: string, finder: FileFinder, onFailure: (cause: unkn
 
 export const make = Effect.fn("WorkspaceSearchIndex.make")(function* (cwd: string) {
   const finder = yield* Effect.acquireRelease(createFinder(cwd), (finder) =>
-    Effect.sync(() => finder.destroy()),
+    Effect.try({
+      try: () => finder.destroy(),
+      catch: (cause) => new WorkspaceSearchIndexDestroyFailed({ cwd, cause }),
+    }).pipe(Effect.orDie),
   );
   yield* waitForScan(
     cwd,