diff --git a/.changeset/world-local-windows-unlink-retry.md b/.changeset/world-local-windows-unlink-retry.md
new file mode 100644
index 0000000000..4c44274000
--- /dev/null
+++ b/.changeset/world-local-windows-unlink-retry.md
@@ -0,0 +1,5 @@
+---
+'@workflow/world-local': patch
+---
+
+Retry transient `EPERM` unlink failures on Windows when deleting hook and entity JSON files. A concurrent reader briefly holding a file open made `deleteJSON` throw a share-violation `EPERM`, which surfaced as a failed operation — for example a failed `run.cancel()` while `deleteAllHooksForRun` raced hook polling.
diff --git a/packages/world-local/src/fs.test.ts b/packages/world-local/src/fs.test.ts
index 9670427e19..3ce6389fb8 100644
--- a/packages/world-local/src/fs.test.ts
+++ b/packages/world-local/src/fs.test.ts
@@ -17,6 +17,7 @@ import {
 import { z } from 'zod';
 import {
   assertSafeEntityId,
+  deleteJSON,
   paginatedFileSystemQuery,
   readFirstByte,
   readJSONWithFallback,
@@ -115,6 +116,67 @@ describe('fs utilities', () => {
     });
   });
 
+  describe('deleteJSON', () => {
+    it('deletes the file and tolerates one that is already gone', async () => {
+      const filePath = path.join(testDir, 'victim.json');
+      await fs.writeFile(filePath, '{}');
+
+      await deleteJSON(filePath);
+      await expect(fs.access(filePath)).rejects.toMatchObject({
+        code: 'ENOENT',
+      });
+
+      await expect(deleteJSON(filePath)).resolves.toBeUndefined();
+    });
+
+    it('propagates non-ENOENT unlink failures', async () => {
+      const eisdir = Object.assign(new Error('EISDIR: illegal operation'), {
+        code: 'EISDIR',
+      });
+      vi.spyOn(fs, 'unlink').mockRejectedValue(eisdir);
+
+      await expect(deleteJSON(path.join(testDir, 'x.json'))).rejects.toThrow(
+        'EISDIR'
+      );
+    });
+
+    it('retries transient EPERM unlink failures on Windows', async () => {
+      // On Windows, unlink fails with EPERM while a concurrent reader briefly
+      // holds the file open (e.g. hook polling racing deleteAllHooksForRun).
+      // Re-import the module with the platform stubbed so its module-level
+      // isWindows check takes the retry path.
+      const platform = Object.getOwnPropertyDescriptor(process, 'platform');
+      Object.defineProperty(process, 'platform', { value: 'win32' });
+      vi.resetModules();
+      try {
+        const freshFsModule = await import('./fs.js');
+        const filePath = path.join(testDir, 'locked.json');
+        await fs.writeFile(filePath, '{}');
+
+        const eperm = Object.assign(
+          new Error('EPERM: operation not permitted, unlink'),
+          { code: 'EPERM' }
+        );
+        const unlinkSpy = vi
+          .spyOn(fs, 'unlink')
+          .mockRejectedValueOnce(eperm)
+          .mockRejectedValueOnce(eperm);
+
+        await freshFsModule.deleteJSON(filePath);
+
+        expect(unlinkSpy).toHaveBeenCalledTimes(3);
+        await expect(fs.access(filePath)).rejects.toMatchObject({
+          code: 'ENOENT',
+        });
+      } finally {
+        if (platform) {
+          Object.defineProperty(process, 'platform', platform);
+        }
+        vi.resetModules();
+      }
+    });
+  });
+
   describe('paginatedFileSystemQuery', () => {
     // Simple getCreatedAt function that strips .json and tries to parse as ULID
     const getCreatedAt = (filename: string): Date | null => {
diff --git a/packages/world-local/src/fs.ts b/packages/world-local/src/fs.ts
index 152def44b6..0cd09e8a30 100644
--- a/packages/world-local/src/fs.ts
+++ b/packages/world-local/src/fs.ts
@@ -403,7 +403,12 @@ export async function readFirstByte(
 
 export async function deleteJSON(filePath: string): Promise<void> {
   try {
-    await fs.unlink(filePath);
+    // On Windows, a concurrent reader briefly holding the file open makes
+    // unlink fail with EPERM (share violation), so retry like the other
+    // mutation paths in this module. A reader's window is milliseconds;
+    // without the retry a transient EPERM surfaces as a failed operation
+    // (e.g. run cancellation via deleteAllHooksForRun).
+    await withWindowsRetry(() => fs.unlink(filePath));
   } catch (error) {
     if ((error as any).code !== 'ENOENT') throw error;
   }