diff --git a/packages/core/src/services/gitService.test.ts b/packages/core/src/services/gitService.test.ts
index 7923b7e647..d45dbed407 100644
--- a/packages/core/src/services/gitService.test.ts
+++ b/packages/core/src/services/gitService.test.ts
@@ -60,6 +60,15 @@ vi.mock('os', async (importOriginal) => {
   };
 });
 
+const hoistedMockDebugLogger = vi.hoisted(() => ({
+  debug: vi.fn(),
+  warn: vi.fn(),
+  error: vi.fn(),
+}));
+vi.mock('../utils/debugLogger.js', () => ({
+  debugLogger: hoistedMockDebugLogger,
+}));
+
 describe('GitService', () => {
   let testRootDir: string;
   let projectRoot: string;
@@ -248,6 +257,21 @@ describe('GitService', () => {
       await service.setupShadowGitRepository();
       expect(hoistedMockCommit).not.toHaveBeenCalled();
     });
+
+    it('should handle checkIsRepo failure gracefully and initialize repo', async () => {
+      // Simulate checkIsRepo failing (e.g., on certain Git versions like macOS 2.39.5)
+      hoistedMockCheckIsRepo.mockRejectedValue(
+        new Error('git rev-parse --is-inside-work-tree failed'),
+      );
+      const service = new GitService(projectRoot, storage);
+      await service.setupShadowGitRepository();
+      // Should proceed to initialize the repo since checkIsRepo failed
+      expect(hoistedMockInit).toHaveBeenCalled();
+      // Should log the error using debugLogger
+      expect(hoistedMockDebugLogger.debug).toHaveBeenCalledWith(
+        expect.stringContaining('checkIsRepo failed'),
+      );
+    });
   });
 
   describe('createFileSnapshot', () => {
diff --git a/packages/core/src/services/gitService.ts b/packages/core/src/services/gitService.ts
index cbda1ae1c3..c0c36b2b88 100644
--- a/packages/core/src/services/gitService.ts
+++ b/packages/core/src/services/gitService.ts
@@ -11,6 +11,7 @@ import { spawnAsync } from '../utils/shell-utils.js';
 import type { SimpleGit } from 'simple-git';
 import { simpleGit, CheckRepoActions } from 'simple-git';
 import type { Storage } from '../config/storage.js';
+import { debugLogger } from '../utils/debugLogger.js';
 
 export class GitService {
   private projectRoot: string;
@@ -67,7 +68,16 @@ export class GitService {
     await fs.writeFile(gitConfigPath, gitConfigContent);
 
     const repo = simpleGit(repoDir);
-    const isRepoDefined = await repo.checkIsRepo(CheckRepoActions.IS_REPO_ROOT);
+    let isRepoDefined = false;
+    try {
+      isRepoDefined = await repo.checkIsRepo(CheckRepoActions.IS_REPO_ROOT);
+    } catch (error) {
+      // If checkIsRepo fails (e.g., on certain Git versions like macOS 2.39.5),
+      // log the error and assume repo is not defined, then proceed with initialization
+      debugLogger.debug(
+        `checkIsRepo failed, will initialize repository: ${error instanceof Error ? error.message : String(error)}`,
+      );
+    }
 
     if (!isRepoDefined) {
       await repo.init(false, {