diff --git a/packages/core/src/config/config.test.ts b/packages/core/src/config/config.test.ts
index c9965e87..bb074a71 100644
--- a/packages/core/src/config/config.test.ts
+++ b/packages/core/src/config/config.test.ts
@@ -17,6 +17,7 @@ import {
   createContentGeneratorConfig,
 } from '../core/contentGenerator.js';
 import { GeminiClient } from '../core/client.js';
+import { GitService } from '../services/gitService.js';
 import { loadServerHierarchicalMemory } from '../utils/memoryDiscovery.js';
 
 // Mock dependencies that might be called during Config construction or createServerConfig
@@ -75,6 +76,12 @@ vi.mock('../telemetry/index.js', async (importOriginal) => {
   };
 });
 
+vi.mock('../services/gitService.js', () => {
+  const GitServiceMock = vi.fn();
+  GitServiceMock.prototype.initialize = vi.fn();
+  return { GitService: GitServiceMock };
+});
+
 describe('Server Config (config.ts)', () => {
   const MODEL = 'gemini-pro';
   const SANDBOX: SandboxConfig = {
@@ -108,6 +115,32 @@ describe('Server Config (config.ts)', () => {
     vi.clearAllMocks();
   });
 
+  describe('initialize', () => {
+    it('should throw an error if checkpointing is enabled and GitService fails', async () => {
+      const gitError = new Error('Git is not installed');
+      (GitService.prototype.initialize as Mock).mockRejectedValue(gitError);
+
+      const config = new Config({
+        ...baseParams,
+        checkpointing: true,
+      });
+
+      await expect(config.initialize()).rejects.toThrow(gitError);
+    });
+
+    it('should not throw an error if checkpointing is disabled and GitService fails', async () => {
+      const gitError = new Error('Git is not installed');
+      (GitService.prototype.initialize as Mock).mockRejectedValue(gitError);
+
+      const config = new Config({
+        ...baseParams,
+        checkpointing: false,
+      });
+
+      await expect(config.initialize()).resolves.toBeUndefined();
+    });
+  });
+
   describe('refreshAuth', () => {
     it('should refresh auth and update config', async () => {
       const config = new Config(baseParams);
diff --git a/packages/core/src/config/config.ts b/packages/core/src/config/config.ts
index 7d982385..1b101815 100644
--- a/packages/core/src/config/config.ts
+++ b/packages/core/src/config/config.ts
@@ -259,11 +259,7 @@ export class Config {
     // Initialize centralized FileDiscoveryService
     this.getFileService();
     if (this.getCheckpointingEnabled()) {
-      try {
-        await this.getGitService();
-      } catch {
-        // For now swallow the error, later log it.
-      }
+      await this.getGitService();
     }
     this.toolRegistry = await this.createToolRegistry();
   }
diff --git a/packages/core/src/services/gitService.test.ts b/packages/core/src/services/gitService.test.ts
index d0b991a3..d23b0737 100644
--- a/packages/core/src/services/gitService.test.ts
+++ b/packages/core/src/services/gitService.test.ts
@@ -154,14 +154,6 @@ describe('GitService', () => {
   });
 
   describe('initialize', () => {
-    it('should throw an error if projectRoot is not a Git repository', async () => {
-      hoistedIsGitRepositoryMock.mockReturnValue(false);
-      const service = new GitService(mockProjectRoot);
-      await expect(service.initialize()).rejects.toThrow(
-        'GitService requires a Git repository',
-      );
-    });
-
     it('should throw an error if Git is not available', async () => {
       hoistedMockExec.mockImplementation((command, callback) => {
         callback(new Error('git not found'));
@@ -169,7 +161,7 @@ describe('GitService', () => {
       });
       const service = new GitService(mockProjectRoot);
       await expect(service.initialize()).rejects.toThrow(
-        'GitService requires Git to be installed',
+        'Checkpointing is enabled, but Git is not installed. Please install Git or disable checkpointing to continue.',
       );
     });
 
diff --git a/packages/core/src/services/gitService.ts b/packages/core/src/services/gitService.ts
index bd7b72fd..8b3fe46f 100644
--- a/packages/core/src/services/gitService.ts
+++ b/packages/core/src/services/gitService.ts
@@ -8,7 +8,6 @@ import * as fs from 'fs/promises';
 import * as path from 'path';
 import * as os from 'os';
 import { isNodeError } from '../utils/errors.js';
-import { isGitRepository } from '../utils/gitUtils.js';
 import { exec } from 'node:child_process';
 import { simpleGit, SimpleGit, CheckRepoActions } from 'simple-git';
 import { getProjectHash, GEMINI_DIR } from '../utils/paths.js';
@@ -26,12 +25,11 @@ export class GitService {
   }
 
   async initialize(): Promise<void> {
-    if (!isGitRepository(this.projectRoot)) {
-      throw new Error('GitService requires a Git repository');
-    }
     const gitAvailable = await this.verifyGitAvailability();
     if (!gitAvailable) {
-      throw new Error('GitService requires Git to be installed');
+      throw new Error(
+        'Checkpointing is enabled, but Git is not installed. Please install Git or disable checkpointing to continue.',
+      );
     }
     this.setupShadowGitRepository();
   }