diff --git a/packages/cli/src/ui/hooks/useGeminiStream.ts b/packages/cli/src/ui/hooks/useGeminiStream.ts
index 45344c73..251fad02 100644
--- a/packages/cli/src/ui/hooks/useGeminiStream.ts
+++ b/packages/cli/src/ui/hooks/useGeminiStream.ts
@@ -912,17 +912,31 @@ export const useGeminiStream = (
           }
 
           try {
-            let commitHash = await gitService?.createFileSnapshot(
-              `Snapshot for ${toolCall.request.name}`,
-            );
+            if (!gitService) {
+              onDebugMessage(
+                `Checkpointing is enabled but Git service is not available. Failed to create snapshot for ${filePath}. Ensure Git is installed and working properly.`,
+              );
+              continue;
+            }
+
+            let commitHash: string | undefined;
+            try {
+              commitHash = await gitService.createFileSnapshot(
+                `Snapshot for ${toolCall.request.name}`,
+              );
+            } catch (error) {
+              onDebugMessage(
+                `Failed to create new snapshot: ${getErrorMessage(error)}. Attempting to use current commit.`,
+              );
+            }
 
             if (!commitHash) {
-              commitHash = await gitService?.getCurrentCommitHash();
+              commitHash = await gitService.getCurrentCommitHash();
             }
 
             if (!commitHash) {
               onDebugMessage(
-                `Failed to create snapshot for ${filePath}. Skipping restorable tool call.`,
+                `Failed to create snapshot for ${filePath}. Checkpointing may not be working properly. Ensure Git is installed and the project directory is accessible.`,
               );
               continue;
             }
@@ -959,9 +973,9 @@ export const useGeminiStream = (
             );
           } catch (error) {
             onDebugMessage(
-              `Failed to write restorable tool call file: ${getErrorMessage(
+              `Failed to create checkpoint for ${filePath}: ${getErrorMessage(
                 error,
-              )}`,
+              )}. This may indicate a problem with Git or file system permissions.`,
             );
           }
         }
diff --git a/packages/core/src/services/gitService.ts b/packages/core/src/services/gitService.ts
index f93a5dc6..702df5ae 100644
--- a/packages/core/src/services/gitService.ts
+++ b/packages/core/src/services/gitService.ts
@@ -31,7 +31,13 @@ export class GitService {
         'Checkpointing is enabled, but Git is not installed. Please install Git or disable checkpointing to continue.',
       );
     }
-    this.setupShadowGitRepository();
+    try {
+      await this.setupShadowGitRepository();
+    } catch (error) {
+      throw new Error(
+        `Failed to initialize checkpointing: ${error instanceof Error ? error.message : 'Unknown error'}. Please check that Git is working properly or disable checkpointing.`,
+      );
+    }
   }
 
   verifyGitAvailability(): Promise<boolean> {
@@ -105,10 +111,16 @@ export class GitService {
   }
 
   async createFileSnapshot(message: string): Promise<string> {
-    const repo = this.shadowGitRepository;
-    await repo.add('.');
-    const commitResult = await repo.commit(message);
-    return commitResult.commit;
+    try {
+      const repo = this.shadowGitRepository;
+      await repo.add('.');
+      const commitResult = await repo.commit(message);
+      return commitResult.commit;
+    } catch (error) {
+      throw new Error(
+        `Failed to create checkpoint snapshot: ${error instanceof Error ? error.message : 'Unknown error'}. Checkpointing may not be working properly.`,
+      );
+    }
   }
 
   async restoreProjectFromSnapshot(commitHash: string): Promise<void> {