diff --git a/packages/cli/src/gemini.test.tsx b/packages/cli/src/gemini.test.tsx
index 2784c5694a..90c63651e7 100644
--- a/packages/cli/src/gemini.test.tsx
+++ b/packages/cli/src/gemini.test.tsx
@@ -747,6 +747,60 @@ describe('gemini.tsx main function kitty protocol', () => {
     emitFeedbackSpy.mockRestore();
   });
 
+  it('should start normally with a warning when no sessions found for resume', async () => {
+    const { SessionSelector, SessionError } = await import(
+      './utils/sessionUtils.js'
+    );
+    vi.mocked(SessionSelector).mockImplementation(
+      () =>
+        ({
+          resolveSession: vi
+            .fn()
+            .mockRejectedValue(SessionError.noSessionsFound()),
+        }) as unknown as InstanceType<typeof SessionSelector>,
+    );
+
+    const processExitSpy = vi
+      .spyOn(process, 'exit')
+      .mockImplementation((code) => {
+        throw new MockProcessExitError(code);
+      });
+    const emitFeedbackSpy = vi.spyOn(coreEvents, 'emitFeedback');
+
+    vi.mocked(loadSettings).mockReturnValue(
+      createMockSettings({
+        merged: { advanced: {}, security: { auth: {} }, ui: { theme: 'test' } },
+        workspace: { settings: {} },
+        setValue: vi.fn(),
+        forScope: () => ({ settings: {}, originalSettings: {}, path: '' }),
+      }),
+    );
+
+    vi.mocked(parseArguments).mockResolvedValue({
+      promptInteractive: false,
+      resume: 'latest',
+    } as unknown as CliArgs);
+    vi.mocked(loadCliConfig).mockResolvedValue(
+      createMockConfig({
+        isInteractive: () => true,
+        getQuestion: () => '',
+        getSandbox: () => undefined,
+      }),
+    );
+
+    await main();
+
+    // Should NOT have crashed
+    expect(processExitSpy).not.toHaveBeenCalled();
+    // Should NOT have emitted a feedback error
+    expect(emitFeedbackSpy).not.toHaveBeenCalledWith(
+      'error',
+      expect.stringContaining('Error resuming session'),
+    );
+    processExitSpy.mockRestore();
+    emitFeedbackSpy.mockRestore();
+  });
+
   it.skip('should log error when cleanupExpiredSessions fails', async () => {
     const { cleanupExpiredSessions } = await import(
       './utils/sessionCleanup.js'
@@ -959,13 +1013,18 @@ describe('gemini.tsx main function exit codes', () => {
       resume: 'invalid-session',
     } as unknown as CliArgs);
 
-    vi.mock('./utils/sessionUtils.js', () => ({
-      SessionSelector: vi.fn().mockImplementation(() => ({
-        resolveSession: vi
-          .fn()
-          .mockRejectedValue(new Error('Session not found')),
-      })),
-    }));
+    vi.mock('./utils/sessionUtils.js', async (importOriginal) => {
+      const original =
+        await importOriginal<typeof import('./utils/sessionUtils.js')>();
+      return {
+        ...original,
+        SessionSelector: vi.fn().mockImplementation(() => ({
+          resolveSession: vi
+            .fn()
+            .mockRejectedValue(new Error('Session not found')),
+        })),
+      };
+    });
 
     process.env['GEMINI_API_KEY'] = 'test-key';
     try {
diff --git a/packages/cli/src/gemini.tsx b/packages/cli/src/gemini.tsx
index 6071488542..331ec0c018 100644
--- a/packages/cli/src/gemini.tsx
+++ b/packages/cli/src/gemini.tsx
@@ -84,7 +84,7 @@ import { validateNonInteractiveAuth } from './validateNonInterActiveAuth.js';
 import { checkForUpdates } from './ui/utils/updateCheck.js';
 import { handleAutoUpdate } from './utils/handleAutoUpdate.js';
 import { appEvents, AppEvent } from './utils/events.js';
-import { SessionSelector } from './utils/sessionUtils.js';
+import { SessionError, SessionSelector } from './utils/sessionUtils.js';
 import { SettingsContext } from './ui/contexts/SettingsContext.js';
 import { MouseProvider } from './ui/contexts/MouseContext.js';
 import { StreamingState } from './ui/types.js';
@@ -706,12 +706,24 @@ export async function main() {
         // Use the existing session ID to continue recording to the same session
         config.setSessionId(resumedSessionData.conversation.sessionId);
       } catch (error) {
-        coreEvents.emitFeedback(
-          'error',
-          `Error resuming session: ${error instanceof Error ? error.message : 'Unknown error'}`,
-        );
-        await runExitCleanup();
-        process.exit(ExitCodes.FATAL_INPUT_ERROR);
+        if (
+          error instanceof SessionError &&
+          error.code === 'NO_SESSIONS_FOUND'
+        ) {
+          // No sessions to resume — start a fresh session with a warning
+          startupWarnings.push({
+            id: 'resume-no-sessions',
+            message: error.message,
+            priority: WarningPriority.High,
+          });
+        } else {
+          coreEvents.emitFeedback(
+            'error',
+            `Error resuming session: ${error instanceof Error ? error.message : 'Unknown error'}`,
+          );
+          await runExitCleanup();
+          process.exit(ExitCodes.FATAL_INPUT_ERROR);
+        }
       }
     }
 
diff --git a/packages/cli/src/utils/sessionUtils.test.ts b/packages/cli/src/utils/sessionUtils.test.ts
index 8491f748bd..bcf7c19dfe 100644
--- a/packages/cli/src/utils/sessionUtils.test.ts
+++ b/packages/cli/src/utils/sessionUtils.test.ts
@@ -341,6 +341,29 @@ describe('SessionSelector', () => {
     );
   });
 
+  it('should throw SessionError with NO_SESSIONS_FOUND when resolving latest with no sessions', async () => {
+    // Empty chats directory — no session files
+    const chatsDir = path.join(tmpDir, 'chats');
+    await fs.mkdir(chatsDir, { recursive: true });
+
+    const emptyConfig = {
+      storage: {
+        getProjectTempDir: () => tmpDir,
+      },
+      getSessionId: () => 'current-session-id',
+    } as Partial<Config> as Config;
+
+    const sessionSelector = new SessionSelector(emptyConfig);
+
+    await expect(sessionSelector.resolveSession('latest')).rejects.toSatisfy(
+      (error) => {
+        expect(error).toBeInstanceOf(SessionError);
+        expect((error as SessionError).code).toBe('NO_SESSIONS_FOUND');
+        return true;
+      },
+    );
+  });
+
   it('should not list sessions with only system messages', async () => {
     const sessionIdWithUser = randomUUID();
     const sessionIdSystemOnly = randomUUID();
diff --git a/packages/cli/src/utils/sessionUtils.ts b/packages/cli/src/utils/sessionUtils.ts
index 7bf05fe94a..ac6987f933 100644
--- a/packages/cli/src/utils/sessionUtils.ts
+++ b/packages/cli/src/utils/sessionUtils.ts
@@ -463,7 +463,7 @@ export class SessionSelector {
       const sessions = await this.listSessions();
 
       if (sessions.length === 0) {
-        throw new Error('No previous sessions found for this project.');
+        throw SessionError.noSessionsFound();
       }
 
       // Sort by startTime (oldest first, so newest sessions get highest numbers)