import crypto from 'crypto';

import bcrypt from 'bcrypt';
import gql from 'graphql-tag';
import request from 'supertest';
import { makeMetadataAPIRequest } from 'test/integration/metadata/suites/utils/make-metadata-api-request.util';
import { assertIsDefinedOrThrow, base64UrlEncode } from 'twenty-shared/utils';
import { type DataSource } from 'typeorm';

import { AppTokenType } from 'src/engine/core-modules/app-token/app-token.entity';
import { SEED_APPLE_WORKSPACE_ID } from 'src/engine/workspace-manager/dev-seeder/core/constants/seeder-workspaces.constant';
import { USER_DATA_SEED_IDS } from 'src/engine/workspace-manager/dev-seeder/core/utils/seed-users.util';

const TEST_WORKSPACE_ID = SEED_APPLE_WORKSPACE_ID;
const TEST_USER_ID = USER_DATA_SEED_IDS.JANE;

type TestRegistration = {
  id: string;
  universalIdentifier: string;
  name: string;
  oAuthClientId: string;
  oAuthRedirectUris: string[];
  oAuthScopes: string[];
};

type TestApplication = {
  id: string;
};

const insertRegistration = async (
  ds: DataSource,
  params: {
    name: string;
    clientSecretHash: string | null;
    redirectUris: string[];
    scopes: string[];
  },
): Promise<TestRegistration> => {
  const id = crypto.randomUUID();
  const universalIdentifier = crypto.randomUUID();
  const oAuthClientId = crypto.randomUUID();

  await ds.query(
    `INSERT INTO core."applicationRegistration"
      (id, "universalIdentifier", name, "oAuthClientId", "oAuthClientSecretHash", "oAuthRedirectUris", "oAuthScopes", "workspaceId")
     VALUES ($1, $2, $3, $4, $5, $6, $7, $8)`,
    [
      id,
      universalIdentifier,
      params.name,
      oAuthClientId,
      params.clientSecretHash,
      params.redirectUris,
      params.scopes,
      TEST_WORKSPACE_ID,
    ],
  );

  return {
    id,
    universalIdentifier,
    name: params.name,
    oAuthClientId,
    oAuthRedirectUris: params.redirectUris,
    oAuthScopes: params.scopes,
  };
};

const insertApplication = async (
  ds: DataSource,
  params: {
    universalIdentifier: string;
    name: string;
    workspaceId: string;
    applicationRegistrationId: string;
  },
): Promise<TestApplication> => {
  const id = crypto.randomUUID();

  await ds.query(
    `INSERT INTO core."application"
      (id, "universalIdentifier", name, "workspaceId", "applicationRegistrationId", "sourceType", "sourcePath", "canBeUninstalled")
     VALUES ($1, $2, $3, $4, $5, 'local', '', true)`,
    [
      id,
      params.universalIdentifier,
      params.name,
      params.workspaceId,
      params.applicationRegistrationId,
    ],
  );

  return { id };
};

const insertAppToken = async (
  ds: DataSource,
  params: {
    value: string;
    type: AppTokenType;
    userId: string;
    workspaceId: string;
    expiresAt: Date;
    context?: Record<string, string>;
  },
): Promise<string> => {
  const rows = await ds.query(
    `INSERT INTO core."appToken"
      (value, type, "userId", "workspaceId", "expiresAt", context)
     VALUES ($1, $2, $3, $4, $5, $6)
     RETURNING id`,
    [
      params.value,
      params.type,
      params.userId,
      params.workspaceId,
      params.expiresAt,
      params.context ? JSON.stringify(params.context) : null,
    ],
  );

  return rows[0].id;
};

describe('OAuth (integration)', () => {
  const baseUrl = `http://localhost:${APP_PORT}`;

  let ds: DataSource;

  let testRegistration: TestRegistration;
  let testClientSecret: string;
  let testApplication: TestApplication;

  let publicRegistration: TestRegistration;

  let autoInstallRegistration: TestRegistration;
  let autoInstallClientSecret: string;

  const createdEntityIds: {
    registrations: string[];
    tokens: string[];
    applications: string[];
  } = { registrations: [], tokens: [], applications: [] };

  beforeAll(async () => {
    ds = global.testDataSource;

    testClientSecret = crypto.randomBytes(32).toString('hex');
    const clientSecretHash = await bcrypt.hash(testClientSecret, 10);

    testRegistration = await insertRegistration(ds, {
      name: 'OAuth Integration Test App',
      clientSecretHash,
      redirectUris: ['https://example.com/callback'],
      scopes: ['read', 'write'],
    });
    createdEntityIds.registrations.push(testRegistration.id);

    testApplication = await insertApplication(ds, {
      universalIdentifier: testRegistration.universalIdentifier,
      name: testRegistration.name,
      workspaceId: TEST_WORKSPACE_ID,
      applicationRegistrationId: testRegistration.id,
    });

    publicRegistration = await insertRegistration(ds, {
      name: 'OAuth Public PKCE Test App',
      clientSecretHash: null,
      redirectUris: ['https://example.com/callback'],
      scopes: ['read', 'write'],
    });
    createdEntityIds.registrations.push(publicRegistration.id);

    const publicApplication = await insertApplication(ds, {
      universalIdentifier: publicRegistration.universalIdentifier,
      name: publicRegistration.name,
      workspaceId: TEST_WORKSPACE_ID,
      applicationRegistrationId: publicRegistration.id,
    });
    createdEntityIds.applications.push(publicApplication.id);

    autoInstallClientSecret = crypto.randomBytes(32).toString('hex');
    const autoInstallSecretHash = await bcrypt.hash(
      autoInstallClientSecret,
      10,
    );

    autoInstallRegistration = await insertRegistration(ds, {
      name: 'OAuth Auto-Install Test App',
      clientSecretHash: autoInstallSecretHash,
      redirectUris: ['https://example.com/callback'],
      scopes: ['api'],
    });
    createdEntityIds.registrations.push(autoInstallRegistration.id);
  });

  afterAll(async () => {
    if (createdEntityIds.tokens.length > 0) {
      const placeholders = createdEntityIds.tokens
        .map((_, i) => `$${i + 1}`)
        .join(', ');

      await ds.query(
        `DELETE FROM core."appToken" WHERE id IN (${placeholders})`,
        createdEntityIds.tokens,
      );
    }

    if (createdEntityIds.applications.length > 0) {
      const placeholders = createdEntityIds.applications
        .map((_, i) => `$${i + 1}`)
        .join(', ');

      await ds.query(
        `DELETE FROM core."application" WHERE id IN (${placeholders})`,
        createdEntityIds.applications,
      );
    }

    if (testApplication) {
      await ds.query(`DELETE FROM core."application" WHERE id = $1`, [
        testApplication.id,
      ]);
    }

    if (createdEntityIds.registrations.length > 0) {
      const placeholders = createdEntityIds.registrations
        .map((_, i) => `$${i + 1}`)
        .join(', ');

      await ds.query(
        `DELETE FROM core."applicationRegistration" WHERE id IN (${placeholders})`,
        createdEntityIds.registrations,
      );
    }
  });

  const postToken = (body: Record<string, string>) =>
    request(baseUrl).post('/oauth/token').send(body);

  describe('Discovery endpoint', () => {
    it('should return OAuth authorization server metadata', async () => {
      const res = await request(baseUrl)
        .get('/.well-known/oauth-authorization-server')
        .expect(200);

      expect(res.body.token_endpoint).toContain('/oauth/token');
      expect(res.body.revocation_endpoint).toContain('/oauth/revoke');
      expect(res.body.introspection_endpoint).toContain('/oauth/introspect');
      expect(res.body.grant_types_supported).toEqual(
        expect.arrayContaining([
          'authorization_code',
          'client_credentials',
          'refresh_token',
        ]),
      );
      expect(res.body.code_challenge_methods_supported).toContain('S256');
      expect(res.body.scopes_supported).toBeDefined();
      expect(res.body.response_types_supported).toContain('code');
    });

    it('should promise `iss` when it serves its own authorization endpoint', async () => {
      const res = await request(baseUrl)
        .get('/.well-known/oauth-authorization-server')
        .expect(200);

      expect(res.body.authorization_endpoint).toBe(
        `${res.body.issuer}/authorize`,
      );
      expect(res.body.authorization_response_iss_parameter_supported).toBe(
        true,
      );
    });
  });

  describe('Authorization endpoint (authorizeApp)', () => {
    const authorizeAppMutation = gql`
      mutation AuthorizeApp(
        $clientId: String!
        $redirectUrl: String!
        $state: String
      ) {
        authorizeApp(
          clientId: $clientId
          redirectUrl: $redirectUrl
          state: $state
        ) {
          redirectUrl
        }
      }
    `;

    it('should return an `iss` matching the advertised issuer alongside code and state', async () => {
      const state = 'integration-state-123';

      const response = await makeMetadataAPIRequest({
        query: authorizeAppMutation,
        variables: {
          clientId: testRegistration.oAuthClientId,
          redirectUrl: testRegistration.oAuthRedirectUris[0],
          state,
        },
      });

      expect(response.body.errors).toBeUndefined();

      const callbackUrl = new URL(response.body.data.authorizeApp.redirectUrl);
      const code = callbackUrl.searchParams.get('code');

      const metadata = await request(baseUrl)
        .get('/.well-known/oauth-authorization-server')
        .expect(200);

      expect(`${callbackUrl.origin}${callbackUrl.pathname}`).toBe(
        testRegistration.oAuthRedirectUris[0],
      );
      expect(code).toMatch(/^[0-9a-f]+$/);
      expect(callbackUrl.searchParams.get('iss')).toBe(metadata.body.issuer);
      expect(callbackUrl.searchParams.get('state')).toBe(state);

      assertIsDefinedOrThrow(code);

      const [issuedToken] = await ds.query(
        `SELECT id FROM core."appToken" WHERE value = $1`,
        [crypto.createHash('sha256').update(code).digest('hex')],
      );

      createdEntityIds.tokens.push(issuedToken.id);
    });
  });

  describe('Token endpoint validation', () => {
    it('should return 400 for unsupported grant_type', async () => {
      const res = await postToken({
        grant_type: 'password',
        client_id: testRegistration.oAuthClientId,
      }).expect(400);

      expect(res.body.error).toBe('unsupported_grant_type');
    });

    it('should return 401 for invalid client_id', async () => {
      const res = await postToken({
        grant_type: 'client_credentials',
        client_id: 'non-existent-client',
        client_secret: testClientSecret,
      }).expect(401);

      expect(res.body.error).toBe('invalid_client');
    });

    it('should return 401 for invalid client_secret', async () => {
      const res = await postToken({
        grant_type: 'client_credentials',
        client_id: testRegistration.oAuthClientId,
        client_secret: 'wrong-secret',
      }).expect(401);

      expect(res.body.error).toBe('invalid_client');
    });

    it('should include Cache-Control: no-store header on responses', async () => {
      const res = await postToken({
        grant_type: 'client_credentials',
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(200);

      expect(res.headers['cache-control']).toBe('no-store');
      expect(res.headers['pragma']).toBe('no-cache');
    });

    it('should return 400 when grant_type is missing', async () => {
      await postToken({
        client_id: testRegistration.oAuthClientId,
      }).expect(400);
    });
  });

  describe('Client credentials grant', () => {
    it('should issue an access token for valid credentials', async () => {
      const res = await postToken({
        grant_type: 'client_credentials',
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(200);

      expect(res.body.access_token).toBeDefined();
      expect(res.body.token_type).toBe('Bearer');
      expect(res.body.expires_in).toBeGreaterThan(0);
      expect(res.body.scope).toBe('read write');
      expect(res.body.refresh_token).toBeUndefined();
    });
  });

  describe('Authorization code grant', () => {
    const createAuthorizationCode = async (
      clientId: string,
      redirectUri = 'https://example.com/callback',
    ): Promise<string> => {
      const code = crypto.randomBytes(42).toString('hex');
      const hashedCode = crypto.createHash('sha256').update(code).digest('hex');

      const tokenId = await insertAppToken(ds, {
        value: hashedCode,
        type: AppTokenType.AuthorizationCode,
        userId: TEST_USER_ID,
        workspaceId: TEST_WORKSPACE_ID,
        expiresAt: new Date(Date.now() + 5 * 60 * 1000),
        context: { redirectUri, clientId },
      });

      createdEntityIds.tokens.push(tokenId);

      return code;
    };

    it('should exchange a valid authorization code for tokens', async () => {
      const code = await createAuthorizationCode(
        testRegistration.oAuthClientId,
      );

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      expect(res.body.access_token).toBeDefined();
      expect(res.body.refresh_token).toBeDefined();
      expect(res.body.token_type).toBe('Bearer');
      expect(res.body.expires_in).toBeGreaterThan(0);
    });

    it('should reject a reused authorization code', async () => {
      const code = await createAuthorizationCode(
        testRegistration.oAuthClientId,
      );

      await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
    });

    it('should reject an expired authorization code', async () => {
      const code = crypto.randomBytes(42).toString('hex');
      const hashedCode = crypto.createHash('sha256').update(code).digest('hex');

      const tokenId = await insertAppToken(ds, {
        value: hashedCode,
        type: AppTokenType.AuthorizationCode,
        userId: TEST_USER_ID,
        workspaceId: TEST_WORKSPACE_ID,
        expiresAt: new Date(Date.now() - 1000),
        context: { clientId: testRegistration.oAuthClientId },
      });

      createdEntityIds.tokens.push(tokenId);

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
    });

    it('should reject when redirect_uri does not match', async () => {
      const code = await createAuthorizationCode(
        testRegistration.oAuthClientId,
      );

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://evil.com/callback',
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
    });

    it('should reject when auth code was issued to a different client', async () => {
      const code = await createAuthorizationCode(
        autoInstallRegistration.oAuthClientId,
      );

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
      expect(res.body.error_description).toContain('not issued to this client');
    });

    it('should require either client_secret or code_verifier', async () => {
      const code = await createAuthorizationCode(
        publicRegistration.oAuthClientId,
      );

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: publicRegistration.oAuthClientId,
        redirect_uri: 'https://example.com/callback',
      }).expect(400);

      expect(res.body.error).toBe('invalid_request');
    });
  });

  describe('Authorization code grant with PKCE', () => {
    const createAuthCodeWithPkce = async (
      clientId: string,
    ): Promise<{
      code: string;
      codeVerifier: string;
    }> => {
      const codeVerifier = crypto.randomBytes(32).toString('hex');
      const codeChallenge = base64UrlEncode(
        crypto.createHash('sha256').update(codeVerifier).digest(),
      );

      const code = crypto.randomBytes(42).toString('hex');
      const hashedCode = crypto.createHash('sha256').update(code).digest('hex');

      const codeTokenId = await insertAppToken(ds, {
        value: hashedCode,
        type: AppTokenType.AuthorizationCode,
        userId: TEST_USER_ID,
        workspaceId: TEST_WORKSPACE_ID,
        expiresAt: new Date(Date.now() + 5 * 60 * 1000),
        context: {
          redirectUri: 'https://example.com/callback',
          clientId,
          codeChallenge,
        },
      });

      createdEntityIds.tokens.push(codeTokenId);

      return { code, codeVerifier };
    };

    it('should exchange code with valid PKCE verifier', async () => {
      const { code, codeVerifier } = await createAuthCodeWithPkce(
        publicRegistration.oAuthClientId,
      );

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: publicRegistration.oAuthClientId,
        code_verifier: codeVerifier,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      expect(res.body.access_token).toBeDefined();
      expect(res.body.refresh_token).toBeDefined();
      expect(res.body.token_type).toBe('Bearer');
    });

    it('should reject code with wrong PKCE verifier', async () => {
      const { code } = await createAuthCodeWithPkce(
        publicRegistration.oAuthClientId,
      );

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: publicRegistration.oAuthClientId,
        code_verifier: 'wrong-verifier',
        redirect_uri: 'https://example.com/callback',
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
    });

    it('should require code_verifier when PKCE was used in authorization', async () => {
      const { code } = await createAuthCodeWithPkce(
        publicRegistration.oAuthClientId,
      );

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: publicRegistration.oAuthClientId,
        redirect_uri: 'https://example.com/callback',
      }).expect(400);

      expect(res.body.error).toBe('invalid_request');
      expect(res.body.error_description).toContain('code_verifier is required');
    });

    it('should reject a confidential client that presents only PKCE and no client_secret', async () => {
      const { code, codeVerifier } = await createAuthCodeWithPkce(
        testRegistration.oAuthClientId,
      );

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        code_verifier: codeVerifier,
        redirect_uri: 'https://example.com/callback',
      }).expect(401);

      expect(res.body.error).toBe('invalid_client');
    });
  });

  describe('OAuth auto-install', () => {
    const createAutoInstallAuthCode = async (): Promise<string> => {
      const code = crypto.randomBytes(42).toString('hex');
      const hashedCode = crypto.createHash('sha256').update(code).digest('hex');

      const tokenId = await insertAppToken(ds, {
        value: hashedCode,
        type: AppTokenType.AuthorizationCode,
        userId: TEST_USER_ID,
        workspaceId: TEST_WORKSPACE_ID,
        expiresAt: new Date(Date.now() + 5 * 60 * 1000),
        context: {
          redirectUri: 'https://example.com/callback',
          clientId: autoInstallRegistration.oAuthClientId,
        },
      });

      createdEntityIds.tokens.push(tokenId);

      return code;
    };

    it('should auto-install application during authorization code exchange', async () => {
      const code = await createAutoInstallAuthCode();

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: autoInstallRegistration.oAuthClientId,
        client_secret: autoInstallClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      expect(res.body.access_token).toBeDefined();
      expect(res.body.refresh_token).toBeDefined();
      expect(res.body.token_type).toBe('Bearer');
      expect(res.body.scope).toBe('api');

      const rows = await ds.query(
        `SELECT id, name, description, "sourcePath", "universalIdentifier"
         FROM core."application"
         WHERE "applicationRegistrationId" = $1
           AND "workspaceId" = $2`,
        [autoInstallRegistration.id, TEST_WORKSPACE_ID],
      );

      expect(rows).toHaveLength(1);

      const autoCreatedApp = rows[0];

      expect(autoCreatedApp.name).toBe('OAuth Auto-Install Test App');
      expect(autoCreatedApp.sourcePath).toBe('oauth-install');
      expect(autoCreatedApp.universalIdentifier).toBe(
        autoInstallRegistration.universalIdentifier,
      );

      createdEntityIds.applications.push(autoCreatedApp.id);
    });

    it('should reuse existing application on subsequent authorization code exchanges', async () => {
      const code = await createAutoInstallAuthCode();

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: autoInstallRegistration.oAuthClientId,
        client_secret: autoInstallClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      expect(res.body.access_token).toBeDefined();

      const rows = await ds.query(
        `SELECT id FROM core."application"
         WHERE "applicationRegistrationId" = $1
           AND "workspaceId" = $2`,
        [autoInstallRegistration.id, TEST_WORKSPACE_ID],
      );

      expect(rows).toHaveLength(1);
    });

    it('should fail client credentials when app is not installed in any workspace', async () => {
      const noInstallSecret = crypto.randomBytes(32).toString('hex');
      const noInstallHash = await bcrypt.hash(noInstallSecret, 10);

      const noInstallRegistration = await insertRegistration(ds, {
        name: 'No Install Test App',
        clientSecretHash: noInstallHash,
        redirectUris: [],
        scopes: ['api'],
      });

      createdEntityIds.registrations.push(noInstallRegistration.id);

      const res = await postToken({
        grant_type: 'client_credentials',
        client_id: noInstallRegistration.oAuthClientId,
        client_secret: noInstallSecret,
      }).expect(400);

      expect(res.body.error).toBe('server_error');
      expect(res.body.error_description).toContain(
        'No workspace installation found',
      );
    });
  });

  describe('Refresh token grant', () => {
    const createRefreshTokenAuthCode = async (
      clientId: string,
    ): Promise<string> => {
      const code = crypto.randomBytes(42).toString('hex');
      const hashedCode = crypto.createHash('sha256').update(code).digest('hex');

      const tokenId = await insertAppToken(ds, {
        value: hashedCode,
        type: AppTokenType.AuthorizationCode,
        userId: TEST_USER_ID,
        workspaceId: TEST_WORKSPACE_ID,
        expiresAt: new Date(Date.now() + 5 * 60 * 1000),
        context: {
          redirectUri: 'https://example.com/callback',
          clientId,
        },
      });

      createdEntityIds.tokens.push(tokenId);

      return code;
    };

    it('should issue new tokens from a valid refresh token', async () => {
      const code = await createRefreshTokenAuthCode(
        testRegistration.oAuthClientId,
      );

      const authCodeRes = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      const refreshToken = authCodeRes.body.refresh_token;

      expect(refreshToken).toBeDefined();

      const res = await postToken({
        grant_type: 'refresh_token',
        refresh_token: refreshToken,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(200);

      expect(res.body.access_token).toBeDefined();
      expect(res.body.refresh_token).toBeDefined();
      expect(res.body.token_type).toBe('Bearer');
      expect(res.body.expires_in).toBeGreaterThan(0);
    });

    it('should reject refresh token presented by a different client', async () => {
      const code = await createRefreshTokenAuthCode(
        testRegistration.oAuthClientId,
      );

      const authCodeRes = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      const refreshToken = authCodeRes.body.refresh_token;

      const res = await postToken({
        grant_type: 'refresh_token',
        refresh_token: refreshToken,
        client_id: autoInstallRegistration.oAuthClientId,
        client_secret: autoInstallClientSecret,
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
      expect(res.body.error_description).toContain('not issued to this client');
    });

    it('should reject an invalid refresh token', async () => {
      const res = await postToken({
        grant_type: 'refresh_token',
        refresh_token: 'invalid-refresh-token',
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
    });
  });

  describe('Authorization code replay detection', () => {
    it('should return specific error when a used code is replayed', async () => {
      const code = crypto.randomBytes(42).toString('hex');
      const hashedCode = crypto.createHash('sha256').update(code).digest('hex');

      const tokenId = await insertAppToken(ds, {
        value: hashedCode,
        type: AppTokenType.AuthorizationCode,
        userId: TEST_USER_ID,
        workspaceId: TEST_WORKSPACE_ID,
        expiresAt: new Date(Date.now() + 5 * 60 * 1000),
        context: {
          redirectUri: 'https://example.com/callback',
          clientId: testRegistration.oAuthClientId,
        },
      });

      createdEntityIds.tokens.push(tokenId);

      await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
      expect(res.body.error_description).toContain('already been used');
    });
  });

  describe('Token revocation endpoint', () => {
    it('should return 200 for valid token revocation', async () => {
      const code = crypto.randomBytes(42).toString('hex');
      const hashedCode = crypto.createHash('sha256').update(code).digest('hex');

      const tokenId = await insertAppToken(ds, {
        value: hashedCode,
        type: AppTokenType.AuthorizationCode,
        userId: TEST_USER_ID,
        workspaceId: TEST_WORKSPACE_ID,
        expiresAt: new Date(Date.now() + 5 * 60 * 1000),
        context: {
          redirectUri: 'https://example.com/callback',
          clientId: testRegistration.oAuthClientId,
        },
      });

      createdEntityIds.tokens.push(tokenId);

      const tokenRes = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      await request(baseUrl)
        .post('/oauth/revoke')
        .send({
          token: tokenRes.body.refresh_token,
          client_id: testRegistration.oAuthClientId,
          client_secret: testClientSecret,
        })
        .expect(200);
    });

    it('should return 200 for invalid token (per RFC 7009)', async () => {
      await request(baseUrl)
        .post('/oauth/revoke')
        .send({
          token: 'completely-invalid-token',
          client_id: testRegistration.oAuthClientId,
          client_secret: testClientSecret,
        })
        .expect(200);
    });
  });

  describe('Token introspection endpoint', () => {
    it('should return active=true for a valid access token', async () => {
      const res = await postToken({
        grant_type: 'client_credentials',
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(200);

      const introspectRes = await request(baseUrl)
        .post('/oauth/introspect')
        .send({
          token: res.body.access_token,
          client_id: testRegistration.oAuthClientId,
          client_secret: testClientSecret,
        })
        .expect(200);

      expect(introspectRes.body.active).toBe(true);
      expect(introspectRes.body.client_id).toBe(testRegistration.oAuthClientId);
      expect(introspectRes.body.token_type).toBe('Bearer');
    });

    it('should return active=false for an invalid token', async () => {
      const res = await request(baseUrl)
        .post('/oauth/introspect')
        .send({
          token: 'invalid-token',
          client_id: testRegistration.oAuthClientId,
          client_secret: testClientSecret,
        })
        .expect(200);

      expect(res.body.active).toBe(false);
    });

    it('should require client_id', async () => {
      await request(baseUrl)
        .post('/oauth/introspect')
        .send({ token: 'some-token' })
        .expect(401);
    });
  });

  describe('Per-user authorizations', () => {
    const exchangeForTokens = async (
      scope = 'read write',
    ): Promise<{
      accessToken: string;
      refreshToken: string;
    }> => {
      const code = crypto.randomBytes(42).toString('hex');
      const hashedCode = crypto.createHash('sha256').update(code).digest('hex');

      const tokenId = await insertAppToken(ds, {
        value: hashedCode,
        type: AppTokenType.AuthorizationCode,
        userId: TEST_USER_ID,
        workspaceId: TEST_WORKSPACE_ID,
        expiresAt: new Date(Date.now() + 5 * 60 * 1000),
        context: {
          redirectUri: 'https://example.com/callback',
          clientId: testRegistration.oAuthClientId,
          scope,
        },
      });

      createdEntityIds.tokens.push(tokenId);

      const res = await postToken({
        grant_type: 'authorization_code',
        code,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
        redirect_uri: 'https://example.com/callback',
      }).expect(200);

      return {
        accessToken: res.body.access_token,
        refreshToken: res.body.refresh_token,
      };
    };

    const findAuthorization = async () => {
      const [authorization] = await ds.query(
        `SELECT "scopes", "lastAuthorizedAt", "revokedAt"
         FROM core."applicationAuthorization"
         WHERE "userId" = $1 AND "applicationId" = $2`,
        [TEST_USER_ID, testApplication.id],
      );

      return authorization;
    };

    const deleteAuthorization = () =>
      ds.query(
        `DELETE FROM core."applicationAuthorization"
         WHERE "userId" = $1 AND "applicationId" = $2`,
        [TEST_USER_ID, testApplication.id],
      );

    const revokeRefreshToken = (refreshToken: string) =>
      request(baseUrl)
        .post('/oauth/revoke')
        .send({
          token: refreshToken,
          client_id: testRegistration.oAuthClientId,
          client_secret: testClientSecret,
        })
        .expect(200);

    // 'read' alone, not the registration's full scope list, so the assertion
    // fails if the granted scope is ignored in favour of the declared one.
    it('should record the authorization with the scopes the user granted', async () => {
      await exchangeForTokens('read');

      const authorization = await findAuthorization();

      expect(authorization).toBeDefined();
      expect(authorization.scopes).toEqual(['read']);
      expect(authorization.revokedAt).toBeNull();
    });

    it('should stop the refresh token being redeemed once the authorization is revoked', async () => {
      const { refreshToken } = await exchangeForTokens();

      await revokeRefreshToken(refreshToken);

      expect((await findAuthorization()).revokedAt).not.toBeNull();

      const res = await postToken({
        grant_type: 'refresh_token',
        refresh_token: refreshToken,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
    });

    it('should let the user authorize again after revoking', async () => {
      const { refreshToken: revokedRefreshToken } = await exchangeForTokens();

      await revokeRefreshToken(revokedRefreshToken);

      const { refreshToken } = await exchangeForTokens();

      expect((await findAuthorization()).revokedAt).toBeNull();

      await postToken({
        grant_type: 'refresh_token',
        refresh_token: refreshToken,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(200);
    });

    // Deleting the row leaves a refresh token in the state every token minted
    // before this table existed is in.
    it('should backfill a refresh token that predates the authorization record without inventing a consent', async () => {
      const { refreshToken } = await exchangeForTokens('read write');

      await deleteAuthorization();

      await postToken({
        grant_type: 'refresh_token',
        refresh_token: refreshToken,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(200);

      const authorization = await findAuthorization();

      expect(authorization).toBeDefined();
      expect(authorization.scopes).toBeNull();
      expect(authorization.lastAuthorizedAt).toBeNull();
      expect(authorization.revokedAt).toBeNull();
    });

    it('should keep a refresh token predating the authorization record revoked', async () => {
      const { refreshToken } = await exchangeForTokens();

      await deleteAuthorization();

      await revokeRefreshToken(refreshToken);

      const res = await postToken({
        grant_type: 'refresh_token',
        refresh_token: refreshToken,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
    });

    const LIST_AUTHORIZATIONS_OPERATION = {
      query: gql`
        query CurrentUserApplicationAuthorizations {
          currentUserApplicationAuthorizations {
            id
            applicationId
            applicationName
            scopes
          }
        }
      `,
    };

    const revokeAuthorizationOperation = (
      applicationAuthorizationId: string,
    ) => ({
      query: gql`
        mutation RevokeApplicationAuthorization(
          $applicationAuthorizationId: UUID!
        ) {
          revokeApplicationAuthorization(
            applicationAuthorizationId: $applicationAuthorizationId
          )
        }
      `,
      variables: { applicationAuthorizationId },
    });

    const findListedAuthorization = async (
      token = APPLE_JANE_ADMIN_ACCESS_TOKEN,
    ) => {
      const res = await makeMetadataAPIRequest(
        LIST_AUTHORIZATIONS_OPERATION,
        token,
      );

      expect(res.body.errors).toBeUndefined();

      return res.body.data.currentUserApplicationAuthorizations.find(
        (authorization: { applicationId: string }) =>
          authorization.applicationId === testApplication.id,
      );
    };

    const revokeListedAuthorization = (
      applicationAuthorizationId: string,
      token: string,
    ) =>
      makeMetadataAPIRequest(
        revokeAuthorizationOperation(applicationAuthorizationId),
        token,
      );

    it('should list the authorization to the user who granted it', async () => {
      await exchangeForTokens('read');

      const authorization = await findListedAuthorization();

      expect(authorization).toBeDefined();
      expect(authorization.applicationName).toBe(testRegistration.name);
      expect(authorization.scopes).toEqual(['read']);
    });

    it('should stop the refresh token being redeemed when revoked from the list', async () => {
      const { refreshToken } = await exchangeForTokens();

      const { id } = await findListedAuthorization();

      const revokeResponse = await revokeListedAuthorization(
        id,
        APPLE_JANE_ADMIN_ACCESS_TOKEN,
      );

      expect(revokeResponse.body.errors).toBeUndefined();
      expect(revokeResponse.body.data.revokeApplicationAuthorization).toBe(
        true,
      );

      const res = await postToken({
        grant_type: 'refresh_token',
        refresh_token: refreshToken,
        client_id: testRegistration.oAuthClientId,
        client_secret: testClientSecret,
      }).expect(400);

      expect(res.body.error).toBe('invalid_grant');
      expect(await findListedAuthorization()).toBeUndefined();
    });

    it('should report a repeated revocation as a no-op', async () => {
      await exchangeForTokens();

      const { id } = await findListedAuthorization();

      const firstRevoke = await revokeListedAuthorization(
        id,
        APPLE_JANE_ADMIN_ACCESS_TOKEN,
      );

      expect(firstRevoke.body.data.revokeApplicationAuthorization).toBe(true);

      const secondRevoke = await revokeListedAuthorization(
        id,
        APPLE_JANE_ADMIN_ACCESS_TOKEN,
      );

      expect(secondRevoke.body.data.revokeApplicationAuthorization).toBe(false);
    });

    it('should not let another user see or revoke the authorization', async () => {
      await exchangeForTokens();

      const { id } = await findListedAuthorization();

      expect(
        await findListedAuthorization(APPLE_JONY_MEMBER_ACCESS_TOKEN),
      ).toBeUndefined();

      const revokeResponse = await revokeListedAuthorization(
        id,
        APPLE_JONY_MEMBER_ACCESS_TOKEN,
      );

      expect(revokeResponse.body.data.revokeApplicationAuthorization).toBe(
        false,
      );
      expect((await findAuthorization()).revokedAt).toBeNull();
    });
  });
});