diff --git a/src/cliproxy/quota-fetcher-gemini-cli.ts b/src/cliproxy/quota-fetcher-gemini-cli.ts
index 3fa5987d..bcbd7887 100644
--- a/src/cliproxy/quota-fetcher-gemini-cli.ts
+++ b/src/cliproxy/quota-fetcher-gemini-cli.ts
@@ -114,6 +114,10 @@ interface ManagedResponse {
   viaManagement: boolean;
 }
 
+function getRemainingTimeoutMs(deadlineMs: number): number {
+  return Math.max(1, deadlineMs - Date.now());
+}
+
 /**
  * Extract project ID from account field
  * Input: "user@example.com (cloudaicompanion-abc-123)"
@@ -235,10 +239,13 @@ function isGeminiAuthFileForAccount(file: ManagementAuthFile, accountId: string)
   );
 }
 
-async function findManagedGeminiAuthIndex(accountId: string): Promise<string | number | null> {
+async function findManagedGeminiAuthIndex(
+  accountId: string,
+  timeoutMs: number
+): Promise<string | number | null> {
   const target = getProxyTarget();
   const controller = new AbortController();
-  const timeoutId = setTimeout(() => controller.abort(), MANAGEMENT_API_TIMEOUT_MS);
+  const timeoutId = setTimeout(() => controller.abort(), timeoutMs);
 
   try {
     const response = await fetch(buildProxyUrl(target, '/v0/management/auth-files'), {
@@ -263,16 +270,17 @@ async function findManagedGeminiAuthIndex(accountId: string): Promise<string | n
 async function performManagedGeminiRequest(
   accountId: string,
   url: string,
-  body: string
+  body: string,
+  timeoutMs: number
 ): Promise<ManagedResponse | null> {
-  const authIndex = await findManagedGeminiAuthIndex(accountId);
+  const authIndex = await findManagedGeminiAuthIndex(accountId, timeoutMs);
   if (authIndex === null || authIndex === undefined) {
     return null;
   }
 
   const target = getProxyTarget();
   const controller = new AbortController();
-  const timeoutId = setTimeout(() => controller.abort(), MANAGEMENT_API_TIMEOUT_MS);
+  const timeoutId = setTimeout(() => controller.abort(), timeoutMs);
 
   try {
     const response = await fetch(buildProxyUrl(target, '/v0/management/api-call'), {
@@ -319,15 +327,24 @@ async function performGeminiCliRequest(
   body: string,
   preferManagement = false
 ): Promise<ManagedResponse> {
+  const deadlineMs = Date.now() + MANAGEMENT_API_TIMEOUT_MS;
+  let managementAttempted = false;
+
   if (preferManagement) {
-    const managedResult = await performManagedGeminiRequest(accountId, url, body);
+    managementAttempted = true;
+    const managedResult = await performManagedGeminiRequest(
+      accountId,
+      url,
+      body,
+      getRemainingTimeoutMs(deadlineMs)
+    );
     if (managedResult) {
       return managedResult;
     }
   }
 
   const controller = new AbortController();
-  const timeoutId = setTimeout(() => controller.abort(), MANAGEMENT_API_TIMEOUT_MS);
+  const timeoutId = setTimeout(() => controller.abort(), getRemainingTimeoutMs(deadlineMs));
 
   try {
     const response = await fetch(url, {
@@ -346,7 +363,16 @@ async function performGeminiCliRequest(
       return directResult;
     }
 
-    const managedResult = await performManagedGeminiRequest(accountId, url, body);
+    if (managementAttempted) {
+      return directResult;
+    }
+
+    const managedResult = await performManagedGeminiRequest(
+      accountId,
+      url,
+      body,
+      getRemainingTimeoutMs(deadlineMs)
+    );
     return managedResult ?? directResult;
   } catch (error) {
     clearTimeout(timeoutId);
diff --git a/tests/unit/cliproxy/quota-fetcher-gemini-cli.test.ts b/tests/unit/cliproxy/quota-fetcher-gemini-cli.test.ts
index f4481a43..7fe6aa86 100644
--- a/tests/unit/cliproxy/quota-fetcher-gemini-cli.test.ts
+++ b/tests/unit/cliproxy/quota-fetcher-gemini-cli.test.ts
@@ -714,6 +714,7 @@ describe('Gemini CLI Quota Fetcher', () => {
       expect(managedLookupRequest.url).toBe(MANAGEMENT_AUTH_FILES_URL);
       expect(managedQuotaRequest.url).toBe(MANAGEMENT_API_CALL_URL);
       expect(managedQuotaRequest.body).toContain('"auth_index":"target-auth-index"');
+      expect(managedQuotaRequest.body).toContain('"Authorization":"Bearer $TOKEN$"');
       expect(managedQuotaRequest.body).not.toContain('default-refresh-token');
     });
 
@@ -824,6 +825,80 @@ describe('Gemini CLI Quota Fetcher', () => {
       }
     });
 
+    it('does not retry the management API twice when the preferred managed path already failed', async () => {
+      writeGeminiToken(
+        {
+          type: 'gemini',
+          email: 'managed-failure@example.com',
+          project_id: 'managed-failure-project',
+          token: {
+            access_token: 'expired-token',
+            refresh_token: 'refresh-token',
+            expiry: Date.now() - 1000,
+          },
+        },
+        'gemini-managed-failure.json'
+      );
+
+      mockFetch([
+        {
+          url: GEMINI_CODE_ASSIST_URL,
+          method: 'POST',
+          status: 503,
+          response: { error: { message: 'supplementary unavailable' } },
+        },
+      ]);
+
+      const originalFetch = globalThis.fetch;
+      let directQuotaAttempt = 0;
+      let managedLookupAttempt = 0;
+      let managedRequestAttempt = 0;
+      globalThis.fetch = (async (input: RequestInfo | URL, init?: RequestInit) => {
+        const url =
+          typeof input === 'string' ? input : input instanceof URL ? input.href : input.url;
+
+        if (url === MANAGEMENT_AUTH_FILES_URL) {
+          managedLookupAttempt += 1;
+          return new Response('lookup unavailable', { status: 503 });
+        }
+
+        if (url === MANAGEMENT_API_CALL_URL) {
+          managedRequestAttempt += 1;
+          return new Response('should not be called', { status: 500 });
+        }
+
+        if (url === GEMINI_QUOTA_URL) {
+          directQuotaAttempt += 1;
+          return new Response(
+            JSON.stringify({
+              error: {
+                message: 'Session expired',
+                status: 'UNAUTHENTICATED',
+              },
+            }),
+            {
+              status: 401,
+              headers: { 'Content-Type': 'application/json' },
+            }
+          );
+        }
+
+        return originalFetch(input, init);
+      }) as typeof fetch;
+
+      try {
+        const result = await fetchGeminiCliQuota('managed-failure@example.com');
+
+        expect(result.success).toBe(false);
+        expect(result.needsReauth).toBe(true);
+        expect(directQuotaAttempt).toBe(1);
+        expect(managedLookupAttempt).toBe(1);
+        expect(managedRequestAttempt).toBe(0);
+      } finally {
+        globalThis.fetch = originalFetch;
+      }
+    });
+
     it('classifies model capacity exhaustion separately from generic rate limits', async () => {
       writeActiveGeminiAccount('capacity@example.com');