@vellumai/assistant 0.4.49 → 0.4.51

package/src/__tests__/oauth-cli.test.ts

@@ -30,6 +30,56 @@ let disconnectOAuthProviderResult: "disconnected" | "not-found" | "error" =
   "not-found";
 let idCounter = 0;
 
+// App upsert mock state
+let mockUpsertAppCalls: Array<{
+  provider: string;
+  clientId: string;
+  clientSecretOpts?: {
+    clientSecretValue?: string;
+    clientSecretCredentialPath?: string;
+  };
+}> = [];
+let mockUpsertAppResult: Record<string, unknown> = {
+  id: "app-upsert-1",
+  providerKey: "integration:test",
+  clientId: "test-client-id",
+  createdAt: 1700000000000,
+  updatedAt: 1700000000000,
+};
+let mockUpsertAppImpl:
+  | ((
+      provider: string,
+      clientId: string,
+      clientSecretOpts?: {
+        clientSecretValue?: string;
+        clientSecretCredentialPath?: string;
+      },
+    ) => Promise<Record<string, unknown>>)
+  | undefined;
+
+// Connect mock state
+let mockOrchestrateOAuthConnect: (
+  opts: Record<string, unknown>,
+) => Promise<Record<string, unknown>>;
+let mockGetAppByProviderAndClientId: (
+  providerKey: string,
+  clientId: string,
+) => Record<string, unknown> | undefined = () => undefined;
+let mockGetMostRecentAppByProvider: (
+  providerKey: string,
+) => Record<string, unknown> | undefined = () => undefined;
+let mockGetProvider: (
+  providerKey: string,
+) => Record<string, unknown> | undefined = () => undefined;
+let mockGetProviderBehavior: (
+  providerKey: string,
+) => Record<string, unknown> | undefined = () => undefined;
+let mockGetSecureKey: (account: string) => string | undefined = () => undefined;
+let mockGetCredentialMetadata: (
+  service: string,
+  field: string,
+) => Record<string, unknown> | undefined = () => undefined;
+
 function nextUUID(): string {
   idCounter += 1;
   return `00000000-0000-0000-0000-${String(idCounter).padStart(12, "0")}`;
@@ -72,13 +122,28 @@ mock.module("../oauth/oauth-store.js", () => ({
   listConnections: () => [],
   deleteConnection: () => false,
   // Stubs required by apps.ts and providers.ts (transitively loaded via oauth/index.ts)
-  upsertApp: async () => ({}),
+  upsertApp: async (
+    provider: string,
+    clientId: string,
+    clientSecretOpts?: {
+      clientSecretValue?: string;
+      clientSecretCredentialPath?: string;
+    },
+  ) => {
+    if (mockUpsertAppImpl) {
+      return mockUpsertAppImpl(provider, clientId, clientSecretOpts);
+    }
+    mockUpsertAppCalls.push({ provider, clientId, clientSecretOpts });
+    return mockUpsertAppResult;
+  },
   getApp: () => undefined,
-  getAppByProviderAndClientId: () => undefined,
-  getMostRecentAppByProvider: () => undefined,
+  getAppByProviderAndClientId: (providerKey: string, clientId: string) =>
+    mockGetAppByProviderAndClientId(providerKey, clientId),
+  getMostRecentAppByProvider: (providerKey: string) =>
+    mockGetMostRecentAppByProvider(providerKey),
   listApps: () => [],
   deleteApp: async () => false,
-  getProvider: () => undefined,
+  getProvider: (providerKey: string) => mockGetProvider(providerKey),
   listProviders: () => mockListProviders(),
   registerProvider: () => ({}),
   seedProviders: () => {},
@@ -89,7 +154,7 @@ mock.module("../oauth/oauth-store.js", () => ({
 
 // Stub out transitive dependencies that token-manager would normally pull in
 mock.module("../security/secure-keys.js", () => ({
-  getSecureKey: () => undefined,
+  getSecureKey: (account: string) => mockGetSecureKey(account),
   setSecureKey: () => true,
   getSecureKeyAsync: async () => undefined,
   setSecureKeyAsync: async () => true,
@@ -116,7 +181,8 @@ mock.module("../security/secure-keys.js", () => ({
 
 mock.module("../tools/credentials/metadata-store.js", () => ({
   assertMetadataWritable: () => {},
-  getCredentialMetadata: () => undefined,
+  getCredentialMetadata: (service: string, field: string) =>
+    mockGetCredentialMetadata(service, field),
   upsertCredentialMetadata: () => ({}),
   listCredentialMetadata: () => [],
   deleteCredentialMetadata: (service: string, field: string): boolean => {
@@ -129,6 +195,25 @@ mock.module("../tools/credentials/metadata-store.js", () => ({
   },
 }));
 
+// ---------------------------------------------------------------------------
+// Mock connect-orchestrator
+// ---------------------------------------------------------------------------
+
+mock.module("../oauth/connect-orchestrator.js", () => ({
+  orchestrateOAuthConnect: (opts: Record<string, unknown>) =>
+    mockOrchestrateOAuthConnect(opts),
+}));
+
+// ---------------------------------------------------------------------------
+// Mock provider-behaviors
+// ---------------------------------------------------------------------------
+
+mock.module("../oauth/provider-behaviors.js", () => ({
+  resolveService: (service: string) => service,
+  getProviderBehavior: (providerKey: string) =>
+    mockGetProviderBehavior(providerKey),
+}));
+
 mock.module("../util/logger.js", () => ({
   getLogger: () => ({
     info: () => {},
@@ -252,11 +337,11 @@ describe("assistant oauth connections token <provider-key>", () => {
     const { exitCode, stdout } = await runCli([
       "connections",
       "token",
-      "integration:gmail",
+      "integration:google",
     ]);
     expect(exitCode).toBe(0);
     expect(stdout).toBe("gmail-token\n");
-    expect(capturedService).toBe("integration:gmail");
+    expect(capturedService).toBe("integration:google");
   });
 
   test("exits 1 when no token exists", async () => {
@@ -336,30 +421,30 @@ describe("assistant oauth connections disconnect <provider-key>", () => {
     const result = await runCli([
       "connections",
       "disconnect",
-      "integration:gmail",
+      "integration:google",
       "--json",
     ]);
     expect(result.exitCode).toBe(0);
     const parsed = JSON.parse(result.stdout);
     expect(parsed.ok).toBe(true);
-    expect(parsed.service).toBe("integration:gmail");
+    expect(parsed.service).toBe("integration:google");
 
     // disconnectOAuthProvider should have been called with the full provider key
-    expect(disconnectOAuthProviderCalls).toEqual(["integration:gmail"]);
+    expect(disconnectOAuthProviderCalls).toEqual(["integration:google"]);
   });
 
   test("reports not-found when nothing exists", async () => {
     const result = await runCli([
       "connections",
       "disconnect",
-      "integration:gmail",
+      "integration:google",
       "--json",
     ]);
     expect(result.exitCode).toBe(1);
     const parsed = JSON.parse(result.stdout);
     expect(parsed.ok).toBe(false);
     expect(parsed.error).toContain("No OAuth connection or credentials");
-    expect(parsed.error).toContain("integration:gmail");
+    expect(parsed.error).toContain("integration:google");
   });
 
   test("cleans up legacy credential keys if present", async () => {
@@ -372,12 +457,12 @@ describe("assistant oauth connections disconnect <provider-key>", () => {
     ];
     for (const field of legacyFields) {
       secureKeyStore.set(
-        credentialKey("integration:gmail", field),
+        credentialKey("integration:google", field),
         `legacy_${field}_value`,
       );
       metadataStore.push({
         credentialId: nextUUID(),
-        service: "integration:gmail",
+        service: "integration:google",
         field,
         allowedTools: [],
         allowedDomains: [],
@@ -389,22 +474,22 @@ describe("assistant oauth connections disconnect <provider-key>", () => {
     const result = await runCli([
       "connections",
       "disconnect",
-      "integration:gmail",
+      "integration:google",
       "--json",
     ]);
     expect(result.exitCode).toBe(0);
     const parsed = JSON.parse(result.stdout);
     expect(parsed.ok).toBe(true);
-    expect(parsed.service).toBe("integration:gmail");
+    expect(parsed.service).toBe("integration:google");
 
     // All legacy keys should be removed
     for (const field of legacyFields) {
       expect(
-        secureKeyStore.has(credentialKey("integration:gmail", field)),
+        secureKeyStore.has(credentialKey("integration:google", field)),
       ).toBe(false);
       expect(
         metadataStore.find(
-          (m) => m.service === "integration:gmail" && m.field === field,
+          (m) => m.service === "integration:google" && m.field === field,
         ),
       ).toBeUndefined();
     }
@@ -416,12 +501,12 @@ describe("assistant oauth connections disconnect <provider-key>", () => {
 
     // Seed a legacy credential key
     secureKeyStore.set(
-      credentialKey("integration:gmail", "access_token"),
+      credentialKey("integration:google", "access_token"),
       "legacy_token",
     );
     metadataStore.push({
       credentialId: nextUUID(),
-      service: "integration:gmail",
+      service: "integration:google",
       field: "access_token",
       allowedTools: [],
       allowedDomains: [],
@@ -432,7 +517,7 @@ describe("assistant oauth connections disconnect <provider-key>", () => {
     const result = await runCli([
       "connections",
       "disconnect",
-      "integration:gmail",
+      "integration:google",
       "--json",
     ]);
     expect(result.exitCode).toBe(0);
@@ -440,9 +525,9 @@ describe("assistant oauth connections disconnect <provider-key>", () => {
     expect(parsed.ok).toBe(true);
 
     // Both should be cleaned up
-    expect(disconnectOAuthProviderCalls).toEqual(["integration:gmail"]);
+    expect(disconnectOAuthProviderCalls).toEqual(["integration:google"]);
     expect(
-      secureKeyStore.has(credentialKey("integration:gmail", "access_token")),
+      secureKeyStore.has(credentialKey("integration:google", "access_token")),
     ).toBe(false);
   });
 });
@@ -454,7 +539,7 @@ describe("assistant oauth connections disconnect <provider-key>", () => {
 describe("assistant oauth providers list", () => {
   const fakeProviders = [
     {
-      providerKey: "integration:gmail",
+      providerKey: "integration:google",
       authUrl: "https://accounts.google.com/o/oauth2/v2/auth",
       tokenUrl: "https://oauth2.googleapis.com/token",
       defaultScopes: "[]",
@@ -511,7 +596,7 @@ describe("assistant oauth providers list", () => {
     const parsed = JSON.parse(stdout);
     expect(parsed).toHaveLength(4);
     const keys = parsed.map((p: { providerKey: string }) => p.providerKey);
-    expect(keys).toContain("integration:gmail");
+    expect(keys).toContain("integration:google");
     expect(keys).toContain("integration:google-calendar");
     expect(keys).toContain("integration:slack");
     expect(keys).toContain("integration:twitter");
@@ -522,13 +607,13 @@ describe("assistant oauth providers list", () => {
       "providers",
       "list",
       "--provider-key",
-      "gmail",
+      "slack",
       "--json",
     ]);
     expect(exitCode).toBe(0);
     const parsed = JSON.parse(stdout);
     expect(parsed).toHaveLength(1);
-    expect(parsed[0].providerKey).toBe("integration:gmail");
+    expect(parsed[0].providerKey).toBe("integration:slack");
   });
 
   test("filters by comma-separated OR values", async () => {
@@ -536,15 +621,16 @@ describe("assistant oauth providers list", () => {
       "providers",
       "list",
       "--provider-key",
-      "gmail,google",
+      "slack,google",
       "--json",
     ]);
     expect(exitCode).toBe(0);
     const parsed = JSON.parse(stdout);
-    expect(parsed).toHaveLength(2);
+    expect(parsed).toHaveLength(3);
     const keys = parsed.map((p: { providerKey: string }) => p.providerKey);
-    expect(keys).toContain("integration:gmail");
+    expect(keys).toContain("integration:google");
     expect(keys).toContain("integration:google-calendar");
+    expect(keys).toContain("integration:slack");
   });
 
   test("returns empty array when comma-separated filter has no matches", async () => {
@@ -559,4 +645,711 @@ describe("assistant oauth providers list", () => {
     const parsed = JSON.parse(stdout);
     expect(parsed).toHaveLength(0);
   });
+
+  test("trims whitespace around commas in --provider-key", async () => {
+    const { exitCode, stdout } = await runCli([
+      "providers",
+      "list",
+      "--provider-key",
+      "slack, google",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    const parsed = JSON.parse(stdout);
+    expect(parsed).toHaveLength(3);
+    const keys = parsed.map((p: { providerKey: string }) => p.providerKey);
+    expect(keys).toContain("integration:google");
+    expect(keys).toContain("integration:google-calendar");
+    expect(keys).toContain("integration:slack");
+  });
+
+  test("ignores empty segments from extra commas in --provider-key", async () => {
+    const { exitCode, stdout } = await runCli([
+      "providers",
+      "list",
+      "--provider-key",
+      "slack,,google",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    const parsed = JSON.parse(stdout);
+    expect(parsed).toHaveLength(3);
+    const keys = parsed.map((p: { providerKey: string }) => p.providerKey);
+    expect(keys).toContain("integration:google");
+    expect(keys).toContain("integration:google-calendar");
+    expect(keys).toContain("integration:slack");
+  });
+});
+
+// ---------------------------------------------------------------------------
+// connect
+// ---------------------------------------------------------------------------
+
+describe("assistant oauth connections connect <provider-key>", () => {
+  beforeEach(() => {
+    mockWithValidToken = async (_service, cb) => cb("mock-access-token-xyz");
+    secureKeyStore = new Map();
+    metadataStore = [];
+    disconnectOAuthProviderCalls = [];
+    disconnectOAuthProviderResult = "not-found";
+    idCounter = 0;
+    mockOrchestrateOAuthConnect = async () => ({
+      success: true,
+      deferred: false,
+      grantedScopes: [],
+    });
+    mockGetAppByProviderAndClientId = () => undefined;
+    mockGetMostRecentAppByProvider = () => undefined;
+    mockGetProvider = () => undefined;
+    mockGetProviderBehavior = () => undefined;
+    mockGetSecureKey = () => undefined;
+  });
+
+  test("completes interactive flow and prints success (human mode)", async () => {
+    mockGetAppByProviderAndClientId = () => ({
+      id: "app-1",
+      clientId: "test-id",
+      clientSecretCredentialPath: "oauth_app/app-1/client_secret",
+      providerKey: "integration:google",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+    mockOrchestrateOAuthConnect = async () => ({
+      success: true,
+      deferred: false,
+      grantedScopes: ["read"],
+      accountInfo: "user@example.com",
+    });
+
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "connect",
+      "integration:google",
+      "--client-id",
+      "test-id",
+    ]);
+    expect(exitCode).toBe(0);
+    expect(stdout).toContain("Connected");
+  });
+
+  test("completes interactive flow and returns JSON with --json flag", async () => {
+    mockGetAppByProviderAndClientId = () => ({
+      id: "app-1",
+      clientId: "test-id",
+      clientSecretCredentialPath: "oauth_app/app-1/client_secret",
+      providerKey: "integration:google",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+    mockOrchestrateOAuthConnect = async () => ({
+      success: true,
+      deferred: false,
+      grantedScopes: ["read"],
+      accountInfo: "user@example.com",
+    });
+
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "connect",
+      "integration:google",
+      "--client-id",
+      "test-id",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    const parsed = JSON.parse(stdout);
+    expect(parsed).toEqual({
+      ok: true,
+      grantedScopes: ["read"],
+      accountInfo: "user@example.com",
+    });
+  });
+
+  test("returns auth URL in default (non-interactive) mode (JSON)", async () => {
+    mockGetAppByProviderAndClientId = () => ({
+      id: "app-1",
+      clientId: "test-id",
+      clientSecretCredentialPath: "oauth_app/app-1/client_secret",
+      providerKey: "integration:google",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+    mockOrchestrateOAuthConnect = async () => ({
+      success: true,
+      deferred: true,
+      authUrl: "https://example.com/auth",
+      state: "abc",
+      service: "integration:google",
+    });
+
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "connect",
+      "integration:google",
+      "--client-id",
+      "test-id",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(true);
+    expect(parsed.deferred).toBe(true);
+    expect(parsed.authUrl).toBe("https://example.com/auth");
+  });
+
+  test("fails when no client_id available", async () => {
+    mockGetMostRecentAppByProvider = () => undefined;
+
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "connect",
+      "integration:google",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toContain("client_id");
+  });
+
+  test("resolves client_id from DB when not provided", async () => {
+    mockGetMostRecentAppByProvider = () => ({
+      id: "app-1",
+      clientId: "db-client-id",
+      clientSecretCredentialPath: "oauth_app/app-1/client_secret",
+      providerKey: "integration:google",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+
+    let capturedClientId: string | undefined;
+    mockOrchestrateOAuthConnect = async (opts) => {
+      capturedClientId = opts.clientId as string;
+      return {
+        success: true,
+        deferred: false,
+        grantedScopes: [],
+      };
+    };
+
+    await runCli(["connections", "connect", "integration:google"]);
+    expect(capturedClientId).toBe("db-client-id");
+  });
+
+  test("resolves client_secret from secure store when not provided", async () => {
+    mockGetMostRecentAppByProvider = () => ({
+      id: "app-1",
+      clientId: "db-client-id",
+      clientSecretCredentialPath: "oauth_app/app-1/client_secret",
+      providerKey: "integration:google",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+
+    mockGetSecureKey = (account: string) =>
+      account === "oauth_app/app-1/client_secret" ? "db-secret" : undefined;
+
+    let capturedOpts: Record<string, unknown> | undefined;
+    mockOrchestrateOAuthConnect = async (opts) => {
+      capturedOpts = opts;
+      return {
+        success: true,
+        deferred: false,
+        grantedScopes: [],
+      };
+    };
+
+    await runCli(["connections", "connect", "integration:google"]);
+    expect(capturedOpts).toBeDefined();
+    expect(capturedOpts!.clientId).toBe("db-client-id");
+    expect(capturedOpts!.clientSecret).toBe("db-secret");
+  });
+
+  test("outputs error from orchestrator", async () => {
+    mockGetAppByProviderAndClientId = () => ({
+      id: "app-1",
+      clientId: "x",
+      clientSecretCredentialPath: "oauth_app/app-1/client_secret",
+      providerKey: "integration:google",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+    mockOrchestrateOAuthConnect = async () => ({
+      success: false,
+      error: "Something went wrong",
+    });
+
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "connect",
+      "integration:google",
+      "--client-id",
+      "x",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toBe("Something went wrong");
+  });
+
+  test("succeeds when callbackTransport is null (loopback default)", async () => {
+    // Provider row has callbackTransport: null — orchestrator should default
+    // to loopback and not require a public ingress URL.
+    mockGetMostRecentAppByProvider = () => ({
+      id: "app-loopback",
+      clientId: "loopback-client",
+      clientSecretCredentialPath: "oauth_app/app-loopback/client_secret",
+      providerKey: "integration:test-loopback",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+
+    let capturedOpts: Record<string, unknown> | undefined;
+    mockOrchestrateOAuthConnect = async (opts) => {
+      capturedOpts = opts;
+      return {
+        success: true,
+        deferred: true,
+        authUrl: "https://example.com/auth?loopback",
+        state: "state-loopback",
+        service: "integration:test-loopback",
+      };
+    };
+
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "connect",
+      "integration:test-loopback",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(true);
+    expect(parsed.deferred).toBe(true);
+    expect(capturedOpts).toBeDefined();
+    expect(capturedOpts!.clientId).toBe("loopback-client");
+  });
+
+  test("returns ingress URL error when callbackTransport is explicitly gateway", async () => {
+    // Provider row has callbackTransport: "gateway" — orchestrator should
+    // require a public ingress URL, which is not configured in the test env.
+    mockGetMostRecentAppByProvider = () => ({
+      id: "app-gateway",
+      clientId: "gateway-client",
+      clientSecretCredentialPath: "oauth_app/app-gateway/client_secret",
+      providerKey: "integration:test-gateway",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+
+    mockOrchestrateOAuthConnect = async () => ({
+      success: false,
+      error:
+        "oauth2_connect from a non-interactive session requires a public ingress URL. Configure ingress.publicBaseUrl first.",
+    });
+
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "connect",
+      "integration:test-gateway",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toContain("requires a public ingress URL");
+  });
+
+  test("fails when client_secret is required but missing", async () => {
+    mockGetAppByProviderAndClientId = () => ({
+      id: "app-1",
+      clientId: "test-id",
+      clientSecretCredentialPath: "oauth_app/app-1/client_secret",
+      providerKey: "integration:google",
+      createdAt: 0,
+      updatedAt: 0,
+    });
+    mockGetProviderBehavior = () => ({
+      setup: {
+        requiresClientSecret: true,
+        displayName: "Test",
+        dashboardUrl: "https://example.com",
+        appType: "app",
+      },
+    });
+
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "connect",
+      "integration:google",
+      "--client-id",
+      "test-id",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toContain("client_secret");
+    expect(parsed.error).toContain("apps upsert");
+  });
+});
+
+// ---------------------------------------------------------------------------
+// apps upsert --client-secret-credential-path
+// ---------------------------------------------------------------------------
+
+describe("assistant oauth apps upsert --client-secret-credential-path", () => {
+  beforeEach(() => {
+    mockWithValidToken = async (_service, cb) => cb("mock-access-token-xyz");
+    secureKeyStore = new Map();
+    metadataStore = [];
+    disconnectOAuthProviderCalls = [];
+    disconnectOAuthProviderResult = "not-found";
+    idCounter = 0;
+    mockUpsertAppCalls = [];
+    mockUpsertAppResult = {
+      id: "app-upsert-1",
+      providerKey: "integration:google",
+      clientId: "abc123",
+      createdAt: 1700000000000,
+      updatedAt: 1700000000000,
+    };
+    mockOrchestrateOAuthConnect = async () => ({
+      success: true,
+      deferred: false,
+      grantedScopes: [],
+    });
+    mockGetAppByProviderAndClientId = () => undefined;
+    mockGetMostRecentAppByProvider = () => undefined;
+    mockGetProvider = () => undefined;
+    mockGetProviderBehavior = () => undefined;
+    mockGetSecureKey = () => undefined;
+    mockGetCredentialMetadata = () => undefined;
+    mockUpsertAppImpl = undefined;
+  });
+
+  test("upsert with --client-secret-credential-path passes path to upsertApp", async () => {
+    const { exitCode, stdout } = await runCli([
+      "apps",
+      "upsert",
+      "--provider",
+      "integration:google",
+      "--client-id",
+      "abc123",
+      "--client-secret-credential-path",
+      "custom/path",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    expect(mockUpsertAppCalls).toHaveLength(1);
+    expect(mockUpsertAppCalls[0]).toEqual({
+      provider: "integration:google",
+      clientId: "abc123",
+      clientSecretOpts: { clientSecretCredentialPath: "custom/path" },
+    });
+    const parsed = JSON.parse(stdout);
+    expect(parsed.id).toBe("app-upsert-1");
+  });
+
+  test("upsert with both --client-secret and --client-secret-credential-path returns error", async () => {
+    const { exitCode, stdout } = await runCli([
+      "apps",
+      "upsert",
+      "--provider",
+      "integration:google",
+      "--client-id",
+      "abc123",
+      "--client-secret",
+      "s3cret",
+      "--client-secret-credential-path",
+      "custom/path",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toContain(
+      "Cannot provide both --client-secret and --client-secret-credential-path",
+    );
+    // upsertApp should NOT have been called
+    expect(mockUpsertAppCalls).toHaveLength(0);
+  });
+
+  test("upsert with --client-secret passes clientSecretValue to upsertApp", async () => {
+    const { exitCode } = await runCli([
+      "apps",
+      "upsert",
+      "--provider",
+      "integration:google",
+      "--client-id",
+      "abc123",
+      "--client-secret",
+      "s3cret",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    expect(mockUpsertAppCalls).toHaveLength(1);
+    expect(mockUpsertAppCalls[0]).toEqual({
+      provider: "integration:google",
+      clientId: "abc123",
+      clientSecretOpts: { clientSecretValue: "s3cret" },
+    });
+  });
+
+  test("upsert without any secret option passes undefined", async () => {
+    const { exitCode } = await runCli([
+      "apps",
+      "upsert",
+      "--provider",
+      "integration:google",
+      "--client-id",
+      "abc123",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    expect(mockUpsertAppCalls).toHaveLength(1);
+    expect(mockUpsertAppCalls[0]).toEqual({
+      provider: "integration:google",
+      clientId: "abc123",
+      clientSecretOpts: undefined,
+    });
+  });
+
+  test("upsert resolves non-prefixed credential path via metadata store", async () => {
+    // The resolution logic splits on the LAST colon, so
+    // "integration:google:client_secret" → service="integration:google", field="client_secret"
+    mockGetCredentialMetadata = (service, field) =>
+      service === "integration:google" && field === "client_secret"
+        ? {
+            credentialId: "cred-1",
+            service: "integration:google",
+            field: "client_secret",
+            allowedTools: [],
+            allowedDomains: [],
+            createdAt: Date.now(),
+            updatedAt: Date.now(),
+          }
+        : undefined;
+
+    const { exitCode, stdout } = await runCli([
+      "apps",
+      "upsert",
+      "--provider",
+      "integration:google",
+      "--client-id",
+      "abc",
+      "--client-secret-credential-path",
+      "integration:google:client_secret",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    expect(mockUpsertAppCalls).toHaveLength(1);
+    // The non-prefixed path should have been resolved to the full credential key
+    expect(mockUpsertAppCalls[0]).toEqual({
+      provider: "integration:google",
+      clientId: "abc",
+      clientSecretOpts: {
+        clientSecretCredentialPath:
+          "credential/integration:google/client_secret",
+      },
+    });
+    const parsed = JSON.parse(stdout);
+    expect(parsed.id).toBe("app-upsert-1");
+  });
+
+  test("upsert passes prefixed credential path through unchanged", async () => {
+    const { exitCode, stdout } = await runCli([
+      "apps",
+      "upsert",
+      "--provider",
+      "integration:google",
+      "--client-id",
+      "abc",
+      "--client-secret-credential-path",
+      "credential/integration:google/client_secret",
+      "--json",
+    ]);
+    expect(exitCode).toBe(0);
+    expect(mockUpsertAppCalls).toHaveLength(1);
+    // Already-prefixed path should be passed through as-is
+    expect(mockUpsertAppCalls[0]).toEqual({
+      provider: "integration:google",
+      clientId: "abc",
+      clientSecretOpts: {
+        clientSecretCredentialPath:
+          "credential/integration:google/client_secret",
+      },
+    });
+    const parsed = JSON.parse(stdout);
+    expect(parsed.id).toBe("app-upsert-1");
+  });
+
+  test("upsert with invalid credential path returns error when no secret found", async () => {
+    // Override upsertApp to throw when given an unresolvable credential path
+    mockUpsertAppImpl = async (_provider, _clientId, clientSecretOpts) => {
+      throw new Error(
+        `No secret found at credential path: ${clientSecretOpts?.clientSecretCredentialPath}`,
+      );
+    };
+
+    const { exitCode, stdout } = await runCli([
+      "apps",
+      "upsert",
+      "--provider",
+      "integration:google",
+      "--client-id",
+      "abc",
+      "--client-secret-credential-path",
+      "bogus:nonexistent:path",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toContain("No secret found");
+  });
+});
+
+// ---------------------------------------------------------------------------
+// ping
+// ---------------------------------------------------------------------------
+
+describe("assistant oauth connections ping <provider-key>", () => {
+  beforeEach(() => {
+    mockWithValidToken = async (_service, cb) => cb("mock-access-token-xyz");
+    secureKeyStore = new Map();
+    metadataStore = [];
+    disconnectOAuthProviderCalls = [];
+    disconnectOAuthProviderResult = "not-found";
+    idCounter = 0;
+  });
+
+  test("returns ok when ping endpoint returns 200", async () => {
+    mockGetProvider = () => ({
+      providerKey: "integration:google",
+      pingUrl: "https://www.googleapis.com/oauth2/v2/userinfo",
+      authUrl: "https://accounts.google.com/o/oauth2/v2/auth",
+      tokenUrl: "https://oauth2.googleapis.com/token",
+      defaultScopes: "[]",
+      scopePolicy: "{}",
+      extraParams: null,
+      createdAt: Date.now(),
+      updatedAt: Date.now(),
+    });
+    const originalFetch = globalThis.fetch;
+    globalThis.fetch = (async () =>
+      new Response("{}", { status: 200 })) as unknown as typeof fetch;
+    try {
+      const { exitCode, stdout } = await runCli([
+        "connections",
+        "ping",
+        "integration:google",
+        "--json",
+      ]);
+      expect(exitCode).toBe(0);
+      const parsed = JSON.parse(stdout);
+      expect(parsed.ok).toBe(true);
+      expect(parsed.status).toBe(200);
+    } finally {
+      globalThis.fetch = originalFetch;
+    }
+  });
+
+  test("exits 1 when provider not found", async () => {
+    mockGetProvider = () => undefined;
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "ping",
+      "integration:unknown",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toContain("Provider not found");
+  });
+
+  test("exits 1 when no ping URL configured", async () => {
+    mockGetProvider = () => ({
+      providerKey: "telegram",
+      pingUrl: null,
+      authUrl: "urn:manual-token",
+      tokenUrl: "urn:manual-token",
+      defaultScopes: "[]",
+      scopePolicy: "{}",
+      extraParams: null,
+      createdAt: Date.now(),
+      updatedAt: Date.now(),
+    });
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "ping",
+      "telegram",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toContain("No ping URL configured");
+  });
+
+  test("exits 1 when ping endpoint returns non-2xx", async () => {
+    mockGetProvider = () => ({
+      providerKey: "integration:google",
+      pingUrl: "https://www.googleapis.com/oauth2/v2/userinfo",
+      authUrl: "https://accounts.google.com/o/oauth2/v2/auth",
+      tokenUrl: "https://oauth2.googleapis.com/token",
+      defaultScopes: "[]",
+      scopePolicy: "{}",
+      extraParams: null,
+      createdAt: Date.now(),
+      updatedAt: Date.now(),
+    });
+    const originalFetch = globalThis.fetch;
+    // Use 403 (not 401) — 401 now throws inside withValidToken for retry
+    globalThis.fetch = (async () =>
+      new Response("Forbidden", { status: 403 })) as unknown as typeof fetch;
+    try {
+      const { exitCode, stdout } = await runCli([
+        "connections",
+        "ping",
+        "integration:google",
+        "--json",
+      ]);
+      expect(exitCode).toBe(1);
+      const parsed = JSON.parse(stdout);
+      expect(parsed.ok).toBe(false);
+      expect(parsed.status).toBe(403);
+    } finally {
+      globalThis.fetch = originalFetch;
+    }
+  });
+
+  test("exits 1 when no token exists", async () => {
+    mockWithValidToken = async () => {
+      throw new Error('No access token found for "integration:google".');
+    };
+    mockGetProvider = () => ({
+      providerKey: "integration:google",
+      pingUrl: "https://www.googleapis.com/oauth2/v2/userinfo",
+      authUrl: "https://accounts.google.com/o/oauth2/v2/auth",
+      tokenUrl: "https://oauth2.googleapis.com/token",
+      defaultScopes: "[]",
+      scopePolicy: "{}",
+      extraParams: null,
+      createdAt: Date.now(),
+      updatedAt: Date.now(),
+    });
+    const { exitCode, stdout } = await runCli([
+      "connections",
+      "ping",
+      "integration:google",
+      "--json",
+    ]);
+    expect(exitCode).toBe(1);
+    const parsed = JSON.parse(stdout);
+    expect(parsed.ok).toBe(false);
+    expect(parsed.error).toContain("No access token");
+  });
 });