diff --git a/src/agents/cli-credentials.test.ts b/src/agents/cli-credentials.test.ts
index 64437d1d6f2..bc1f00a4cda 100644
--- a/src/agents/cli-credentials.test.ts
+++ b/src/agents/cli-credentials.test.ts
@@ -205,7 +205,7 @@ describe("cli credentials", () => {
   it.each([
     {
       name: "caches Claude Code CLI credentials within the TTL window",
-      allowKeychainPromptSecondRead: false,
+      allowKeychainPromptSecondRead: true,
       advanceMs: 0,
       expectedCalls: 1,
       expectSameObject: true,
@@ -240,6 +240,62 @@ describe("cli credentials", () => {
     },
   );
 
+  it("does not let no-keychain Claude cache misses poison keychain reads", async () => {
+    const tempDir = fs.mkdtempSync(path.join(os.tmpdir(), "openclaw-claude-cache-"));
+    vi.setSystemTime(new Date("2025-01-01T00:00:00Z"));
+
+    const withoutKeychain = readClaudeCliCredentialsCached({
+      allowKeychainPrompt: false,
+      ttlMs: CLI_CREDENTIALS_CACHE_TTL_MS,
+      platform: "darwin",
+      homeDir: tempDir,
+      execSync: execSyncMock,
+    });
+
+    expect(withoutKeychain).toBeNull();
+    expect(execSyncMock).not.toHaveBeenCalled();
+
+    mockClaudeCliCredentialRead();
+    const withKeychain = readClaudeCliCredentialsCached({
+      allowKeychainPrompt: true,
+      ttlMs: CLI_CREDENTIALS_CACHE_TTL_MS,
+      platform: "darwin",
+      homeDir: tempDir,
+      execSync: execSyncMock,
+    });
+
+    expect(withKeychain).toMatchObject({
+      type: "oauth",
+      provider: "anthropic",
+      refresh: "cached-refresh",
+    });
+    expect(execSyncMock).toHaveBeenCalledTimes(1);
+  });
+
+  it("reuses cached Claude keychain credentials for no-prompt reads", async () => {
+    const tempDir = fs.mkdtempSync(path.join(os.tmpdir(), "openclaw-claude-cache-"));
+    vi.setSystemTime(new Date("2025-01-01T00:00:00Z"));
+    mockClaudeCliCredentialRead();
+
+    const withKeychain = readClaudeCliCredentialsCached({
+      allowKeychainPrompt: true,
+      ttlMs: CLI_CREDENTIALS_CACHE_TTL_MS,
+      platform: "darwin",
+      homeDir: tempDir,
+      execSync: execSyncMock,
+    });
+    const withoutPrompt = readClaudeCliCredentialsCached({
+      allowKeychainPrompt: false,
+      ttlMs: CLI_CREDENTIALS_CACHE_TTL_MS,
+      platform: "darwin",
+      homeDir: tempDir,
+      execSync: execSyncMock,
+    });
+
+    expect(withoutPrompt).toEqual(withKeychain);
+    expect(execSyncMock).toHaveBeenCalledTimes(1);
+  });
+
   it("reads Codex credentials from keychain when available", async () => {
     const tempHome = fs.mkdtempSync(path.join(os.tmpdir(), "openclaw-codex-"));
     process.env.CODEX_HOME = tempHome;
diff --git a/src/agents/cli-credentials.ts b/src/agents/cli-credentials.ts
index cbe09c65286..fe6ba1c29b8 100644
--- a/src/agents/cli-credentials.ts
+++ b/src/agents/cli-credentials.ts
@@ -455,14 +455,30 @@ export function readClaudeCliCredentialsCached(options?: {
   homeDir?: string;
   execSync?: ExecSyncFn;
 }): ClaudeCliCredential | null {
+  const platform = options?.platform ?? process.platform;
+  const ttlMs = options?.ttlMs ?? 0;
+  const credentialsPath = resolveClaudeCliCredentialsPath(options?.homeDir);
+  const keychainCacheKey = `${credentialsPath}:keychain`;
+  if (
+    ttlMs > 0 &&
+    platform === "darwin" &&
+    options?.allowKeychainPrompt === false &&
+    claudeCliCache?.cacheKey === keychainCacheKey &&
+    claudeCliCache.value &&
+    Date.now() - claudeCliCache.readAt < ttlMs
+  ) {
+    return claudeCliCache.value;
+  }
+  const keychainIntent =
+    platform === "darwin" && options?.allowKeychainPrompt !== false ? "keychain" : "file";
   return readCachedCliCredential({
-    ttlMs: options?.ttlMs ?? 0,
+    ttlMs,
     cache: claudeCliCache,
-    cacheKey: resolveClaudeCliCredentialsPath(options?.homeDir),
+    cacheKey: `${credentialsPath}:${keychainIntent}`,
     read: () =>
       readClaudeCliCredentials({
         allowKeychainPrompt: options?.allowKeychainPrompt,
-        platform: options?.platform,
+        platform,
         homeDir: options?.homeDir,
         execSync: options?.execSync,
       }),