@animus-labs/cortex 0.2.3 → 0.2.4

package/dist/index.d.ts

@@ -51,6 +51,6 @@ export type { CortexModel } from './model-wrapper.js';
 export { inferUtilityModel, inferUtilityModelId } from './utility-model-inference.js';
 export { PROVIDER_REGISTRY, OAUTH_PROVIDER_IDS, UTILITY_MODEL_OVERRIDES, UTILITY_MODEL_DEFAULTS, PRIMARY_MODEL_DEFAULTS, PROVIDER_CACHE_CONFIG, resolveCacheRetention, } from './provider-registry.js';
 export type { AuthMethod, ProviderInfo, ModelInfo, ProviderCacheConfig, CacheRetention, } from './provider-registry.js';
-export { ProviderManager } from './provider-manager.js';
-export type { IProviderManager, OAuthCallbacks, OAuthCallbackPageContext, OAuthCallbackPageRenderer, OAuthCallbackPageStatus, OAuthMeta, OAuthResult, OAuthRefreshResult, CustomModelConfig, ApiKeyValidationStatus, ApiKeyValidationResult, } from './provider-manager.js';
+export { ProviderManager, OAuthError } from './provider-manager.js';
+export type { OAuthErrorCode, IProviderManager, OAuthCallbacks, OAuthCallbackPageContext, OAuthCallbackPageRenderer, OAuthCallbackPageStatus, OAuthMeta, OAuthResult, OAuthRefreshResult, CustomModelConfig, ApiKeyValidationStatus, ApiKeyValidationResult, } from './provider-manager.js';
 //# sourceMappingURL=index.d.ts.map

package/dist/index.d.ts.map

@@ -1 +1 @@
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package/dist/index.js

@@ -54,5 +54,5 @@ export { inferUtilityModel, inferUtilityModelId } from './utility-model-inferenc
 // Provider Registry (Phase 1D)
 export { PROVIDER_REGISTRY, OAUTH_PROVIDER_IDS, UTILITY_MODEL_OVERRIDES, UTILITY_MODEL_DEFAULTS, PRIMARY_MODEL_DEFAULTS, PROVIDER_CACHE_CONFIG, resolveCacheRetention, } from './provider-registry.js';
 // Provider Manager (Phase 1D)
-export { ProviderManager } from './provider-manager.js';
+export { ProviderManager, OAuthError } from './provider-manager.js';
 //# sourceMappingURL=index.js.map

package/dist/index.js.map

@@ -1 +1 @@
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package/dist/provider-manager.d.ts

@@ -62,6 +62,15 @@ export interface OAuthCallbacks {
      * localhost callback routes and is restored immediately after the login flow.
      */
     renderCallbackPage?: OAuthCallbackPageRenderer | undefined;
+    /**
+     * Overall timeout for the OAuth flow, in milliseconds. pi-ai's
+     * callback-server flows (e.g. Anthropic) do not honor an abort signal and
+     * hang forever if the callback never arrives or arrives with an error, so
+     * Cortex enforces this timeout itself and rejects with an
+     * `OAuthError('timed_out')`. Defaults to 5 minutes. Pass `0` or a negative
+     * value to disable (not recommended).
+     */
+    timeoutMs?: number | undefined;
 }
 /** Status of the browser callback page produced by an OAuth flow. */
 export type OAuthCallbackPageStatus = 'success' | 'error';
@@ -132,6 +141,32 @@ export interface OAuthRefreshResult {
     /** Whether the credentials were actually refreshed (true) or reused as-is (false). */
     changed: boolean;
 }
+/**
+ * Discriminant for OAuth flow failures, so consumers can render specific
+ * UX instead of parsing error strings.
+ *
+ * - `unsupported_provider`: provider has no OAuth support.
+ * - `callback_port_in_use`: the provider's fixed loopback callback port is
+ *   already bound (e.g. another Anthropic app on 53692, or a leftover flow).
+ *   Detected before the browser opens.
+ * - `cancelled`: the flow was cancelled via `cancelOAuth()`.
+ * - `timed_out`: the flow exceeded its timeout (pi-ai's callback servers do
+ *   not honor an abort signal, so this is the backstop against hangs).
+ * - `callback_failed`: the browser callback fired but the provider reported
+ *   an error (e.g. state mismatch). Surfaced immediately instead of hanging.
+ */
+export type OAuthErrorCode = 'unsupported_provider' | 'callback_port_in_use' | 'cancelled' | 'timed_out' | 'callback_failed';
+/** Structured error thrown by initiateOAuth. */
+export declare class OAuthError extends Error {
+    readonly code: OAuthErrorCode;
+    readonly provider: string;
+    /** The fixed callback port, when relevant (`callback_port_in_use`). */
+    readonly port?: number | undefined;
+    constructor(code: OAuthErrorCode, provider: string, message: string, options?: {
+        port?: number | undefined;
+        cause?: unknown;
+    });
+}
 /** Configuration for creating a custom model endpoint. */
 export interface CustomModelConfig {
     /** Base URL of the OpenAI-compatible API (e.g., 'http://localhost:11434/v1'). */
@@ -201,7 +236,9 @@ export declare class ProviderManager implements IProviderManager {
      * @param provider - OAuth provider identifier
      * @param callbacks - UI callbacks for auth URL, prompts, and progress
      * @returns The OAuth credentials and display metadata
-     * @throws Error if the provider does not support OAuth or pi-ai is not installed
+     * @throws {OAuthError} `unsupported_provider`, `callback_port_in_use`,
+     *   `cancelled`, `timed_out`, or `callback_failed`. Other errors (e.g.
+     *   network/token-exchange failures from pi-ai) propagate as-is.
      */
     initiateOAuth(provider: string, callbacks: OAuthCallbacks): Promise<OAuthResult>;
     /**

package/dist/provider-manager.d.ts.map

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package/dist/provider-manager.js

@@ -18,28 +18,93 @@ import { createRequire } from 'node:module';
 import { wrapModel } from './model-wrapper.js';
 import { inferUtilityModelId } from './utility-model-inference.js';
 const nodeRequire = createRequire(import.meta.url);
+/** Structured error thrown by initiateOAuth. */
+export class OAuthError extends Error {
+    code;
+    provider;
+    /** The fixed callback port, when relevant (`callback_port_in_use`). */
+    port;
+    constructor(code, provider, message, options) {
+        super(message, options?.cause !== undefined ? { cause: options.cause } : undefined);
+        this.name = 'OAuthError';
+        this.code = code;
+        this.provider = provider;
+        this.port = options?.port;
+    }
+}
 const OAUTH_CALLBACK_ROUTES = {
     anthropic: { path: '/callback', port: 53692 },
     'openai-codex': { path: '/auth/callback', port: 1455 },
 };
 let activeOAuthCallbackPageShim = null;
-async function withOAuthCallbackPageShim(provider, providerName, render, run) {
+/** Ensures `onResult` fires at most once per installed shim. */
+let oauthCallbackResultNotified = false;
+/** Default overall OAuth flow timeout (pi-ai hangs without this). */
+const DEFAULT_OAUTH_FLOW_TIMEOUT_MS = 5 * 60_000;
+/**
+ * Probe whether something is already listening on a loopback port. Used to
+ * fail an OAuth flow fast (before opening a browser) when the provider's
+ * fixed callback port is occupied — otherwise pi-ai binds the other stack /
+ * the browser hits the wrong listener and the user gets a dead page while
+ * pi-ai waits forever.
+ */
+function probeCallbackPortInUse(port, host) {
+    const net = nodeRequire('node:net');
+    return new Promise((resolve) => {
+        let settled = false;
+        const finish = (inUse) => {
+            if (settled)
+                return;
+            settled = true;
+            socket.destroy();
+            resolve(inUse);
+        };
+        const socket = net.connect({ port, host });
+        socket.once('connect', () => finish(true));
+        socket.once('error', () => finish(false));
+        socket.setTimeout(600, () => finish(false));
+    });
+}
+/**
+ * Throw an `OAuthError('callback_port_in_use')` if the provider's fixed
+ * callback port is occupied on either IPv4 or IPv6 loopback. No-op for
+ * providers without a known callback route (manual/device-code flows).
+ */
+async function assertOAuthCallbackPortAvailable(provider) {
     const route = OAUTH_CALLBACK_ROUTES[provider];
-    if (!render || !route) {
-        return run();
+    if (!route)
+        return;
+    for (const host of ['127.0.0.1', '::1']) {
+        if (await probeCallbackPortInUse(route.port, host)) {
+            throw new OAuthError('callback_port_in_use', provider, `OAuth callback port ${route.port} for "${provider}" is already in use ` +
+                `(detected on ${host}). This is a fixed port: another application is ` +
+                `holding it, or a previous sign-in did not finish. Close that ` +
+                `application (or restart the host process), then try again.`, { port: route.port });
+        }
+    }
+}
+/**
+ * Install the callback-page shim for a flow when there is a known callback
+ * route AND something to do with it (a custom renderer and/or a result
+ * observer). Returns a release function (a no-op when no shim was installed).
+ *
+ * Unlike a `try/finally` wrapper around pi-ai's `login()`, the caller owns
+ * the release lifecycle: pi-ai's callback-server flows hang forever on a
+ * non-success callback, so cleanup must be tied to the flow's own
+ * race/timeout, not to awaiting the (possibly never-settling) login promise.
+ */
+function maybeInstallOAuthCallbackShim(provider, providerName, render, onResult) {
+    const route = OAUTH_CALLBACK_ROUTES[provider];
+    if (!route || (!render && !onResult)) {
+        return () => { };
     }
-    const release = installOAuthCallbackPageShim({
+    return installOAuthCallbackPageShim({
         provider,
         providerName,
         route,
         render,
+        onResult,
     });
-    try {
-        return await run();
-    }
-    finally {
-        release();
-    }
 }
 function installOAuthCallbackPageShim(shim) {
     if (activeOAuthCallbackPageShim) {
@@ -49,6 +114,7 @@ function installOAuthCallbackPageShim(shim) {
     const prototype = http.ServerResponse.prototype;
     const previousEnd = prototype.end;
     activeOAuthCallbackPageShim = shim;
+    oauthCallbackResultNotified = false;
     const patchedEnd = function patchedOAuthCallbackEnd(...args) {
         const replacement = maybeRenderOAuthCallbackPage(this, args[0]);
         if (replacement) {
@@ -112,6 +178,20 @@ function maybeRenderOAuthCallbackPage(response, chunk) {
     if (details !== undefined) {
         context.details = details;
     }
+    // Notify the flow that the browser callback fired (once). This lets
+    // initiateOAuth react to a failed callback immediately rather than
+    // waiting on pi-ai, which hangs on non-success callbacks.
+    if (!oauthCallbackResultNotified && shim.onResult) {
+        oauthCallbackResultNotified = true;
+        try {
+            shim.onResult(status, context);
+        }
+        catch {
+            // An observer must never break the callback response.
+        }
+    }
+    if (!shim.render)
+        return null;
     try {
         const rendered = shim.render(context);
         return typeof rendered === 'string' && rendered.trim().length > 0 ? rendered : null;
@@ -427,32 +507,83 @@ export class ProviderManager {
      * @param provider - OAuth provider identifier
      * @param callbacks - UI callbacks for auth URL, prompts, and progress
      * @returns The OAuth credentials and display metadata
-     * @throws Error if the provider does not support OAuth or pi-ai is not installed
+     * @throws {OAuthError} `unsupported_provider`, `callback_port_in_use`,
+     *   `cancelled`, `timed_out`, or `callback_failed`. Other errors (e.g.
+     *   network/token-exchange failures from pi-ai) propagate as-is.
      */
     async initiateOAuth(provider, callbacks) {
         const oauthModule = await loadPiAiOAuth();
         const oauthProvider = oauthModule.getOAuthProvider?.(provider);
         if (!oauthProvider) {
-            throw new Error(`Provider "${provider}" does not support OAuth`);
+            throw new OAuthError('unsupported_provider', provider, `Provider "${provider}" does not support OAuth`);
         }
-        this.activeOAuthAbort = new AbortController();
+        // (A) Fail fast — before opening a browser — if the provider's fixed
+        // callback port is already taken. Otherwise pi-ai binds the other
+        // stack, the browser hits the wrong listener, and pi-ai waits forever.
+        await assertOAuthCallbackPortAvailable(provider);
+        const abort = new AbortController();
+        this.activeOAuthAbort = abort;
+        // (C) pi-ai only settles its callback wait on success; on a failed
+        // callback (e.g. state mismatch) it hangs. The render shim already sees
+        // that response — use it to fail the flow immediately with the reason.
+        let failFromCallback;
+        const callbackFailure = new Promise((_, reject) => {
+            failFromCallback = reject;
+        });
+        const handleCallbackResult = (status, ctx) => {
+            if (status !== 'error')
+                return;
+            const detail = ctx.details ? ` (${ctx.details})` : '';
+            failFromCallback(new OAuthError('callback_failed', provider, `OAuth callback for "${provider}" reported a failure: ${ctx.message}${detail}`));
+        };
+        const releaseShim = maybeInstallOAuthCallbackShim(provider, oauthProvider.name, callbacks.renderCallbackPage, handleCallbackResult);
+        // (B) pi-ai callback servers ignore the abort signal, so cancellation
+        // and timeout are enforced here. Without this the flow hangs forever.
+        const timeoutMs = callbacks.timeoutMs ?? DEFAULT_OAUTH_FLOW_TIMEOUT_MS;
+        let timer;
+        const timeout = new Promise((_, reject) => {
+            if (timeoutMs > 0 && Number.isFinite(timeoutMs)) {
+                timer = setTimeout(() => reject(new OAuthError('timed_out', provider, `OAuth flow for "${provider}" timed out after ${timeoutMs}ms.`)), timeoutMs);
+                timer.unref?.();
+            }
+        });
+        const cancelled = new Promise((_, reject) => {
+            abort.signal.addEventListener('abort', () => reject(new OAuthError('cancelled', provider, `OAuth flow for "${provider}" was cancelled.`)), { once: true });
+        });
+        const login = oauthProvider.login({
+            onAuth: callbacks.onAuth,
+            onPrompt: callbacks.onPrompt,
+            onProgress: callbacks.onProgress,
+            onManualCodeInput: callbacks.onManualCodeInput,
+            onSelect: callbacks.onSelect,
+            signal: abort.signal,
+        });
+        // Whichever promise loses the race may still settle later (pi-ai's
+        // login can hang or settle late; the aux promises can reject after the
+        // race is decided). Attach inert handlers so a late rejection never
+        // surfaces as an unhandled rejection. Promise.race still observes the
+        // first settlement independently.
+        login.catch(() => { });
+        cancelled.catch(() => { });
+        timeout.catch(() => { });
+        callbackFailure.catch(() => { });
         try {
-            const rawCredentials = await withOAuthCallbackPageShim(provider, oauthProvider.name, callbacks.renderCallbackPage, () => oauthProvider.login({
-                onAuth: callbacks.onAuth,
-                onPrompt: callbacks.onPrompt,
-                onProgress: callbacks.onProgress,
-                onManualCodeInput: callbacks.onManualCodeInput,
-                onSelect: callbacks.onSelect,
-                signal: this.activeOAuthAbort.signal,
-            }));
-            this.activeOAuthAbort = null;
+            const rawCredentials = await Promise.race([
+                login,
+                cancelled,
+                timeout,
+                callbackFailure,
+            ]);
             const credentials = JSON.stringify(rawCredentials);
             const meta = buildOAuthMeta(provider, rawCredentials);
             return { credentials, meta };
         }
-        catch (err) {
-            this.activeOAuthAbort = null;
-            throw err;
+        finally {
+            if (timer)
+                clearTimeout(timer);
+            releaseShim();
+            if (this.activeOAuthAbort === abort)
+                this.activeOAuthAbort = null;
         }
     }
     /**

package/dist/provider-manager.js.map

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package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@animus-labs/cortex",
-  "version": "0.2.3",
+  "version": "0.2.4",
   "description": "Production-grade agent framework with structured context management, compaction, tools, and MCP support",
   "license": "MIT",
   "author": "Animus Labs",

package/src/index.ts

@@ -281,8 +281,9 @@ export type {
 } from './provider-registry.js';
 
 // Provider Manager (Phase 1D)
-export { ProviderManager } from './provider-manager.js';
+export { ProviderManager, OAuthError } from './provider-manager.js';
 export type {
+  OAuthErrorCode,
   IProviderManager,
   OAuthCallbacks,
   OAuthCallbackPageContext,

package/src/provider-manager.ts

@@ -75,6 +75,16 @@ export interface OAuthCallbacks {
    * localhost callback routes and is restored immediately after the login flow.
    */
   renderCallbackPage?: OAuthCallbackPageRenderer | undefined;
+
+  /**
+   * Overall timeout for the OAuth flow, in milliseconds. pi-ai's
+   * callback-server flows (e.g. Anthropic) do not honor an abort signal and
+   * hang forever if the callback never arrives or arrives with an error, so
+   * Cortex enforces this timeout itself and rejects with an
+   * `OAuthError('timed_out')`. Defaults to 5 minutes. Pass `0` or a negative
+   * value to disable (not recommended).
+   */
+  timeoutMs?: number | undefined;
 }
 
 /** Status of the browser callback page produced by an OAuth flow. */
@@ -152,6 +162,48 @@ export interface OAuthRefreshResult {
   changed: boolean;
 }
 
+/**
+ * Discriminant for OAuth flow failures, so consumers can render specific
+ * UX instead of parsing error strings.
+ *
+ * - `unsupported_provider`: provider has no OAuth support.
+ * - `callback_port_in_use`: the provider's fixed loopback callback port is
+ *   already bound (e.g. another Anthropic app on 53692, or a leftover flow).
+ *   Detected before the browser opens.
+ * - `cancelled`: the flow was cancelled via `cancelOAuth()`.
+ * - `timed_out`: the flow exceeded its timeout (pi-ai's callback servers do
+ *   not honor an abort signal, so this is the backstop against hangs).
+ * - `callback_failed`: the browser callback fired but the provider reported
+ *   an error (e.g. state mismatch). Surfaced immediately instead of hanging.
+ */
+export type OAuthErrorCode =
+  | 'unsupported_provider'
+  | 'callback_port_in_use'
+  | 'cancelled'
+  | 'timed_out'
+  | 'callback_failed';
+
+/** Structured error thrown by initiateOAuth. */
+export class OAuthError extends Error {
+  readonly code: OAuthErrorCode;
+  readonly provider: string;
+  /** The fixed callback port, when relevant (`callback_port_in_use`). */
+  readonly port?: number | undefined;
+
+  constructor(
+    code: OAuthErrorCode,
+    provider: string,
+    message: string,
+    options?: { port?: number | undefined; cause?: unknown },
+  ) {
+    super(message, options?.cause !== undefined ? { cause: options.cause } : undefined);
+    this.name = 'OAuthError';
+    this.code = code;
+    this.provider = provider;
+    this.port = options?.port;
+  }
+}
+
 /** Configuration for creating a custom model endpoint. */
 export interface CustomModelConfig {
   /** Base URL of the OpenAI-compatible API (e.g., 'http://localhost:11434/v1'). */
@@ -256,7 +308,13 @@ interface ActiveOAuthCallbackPageShim {
   readonly provider: string;
   readonly providerName: string;
   readonly route: OAuthCallbackRoute;
-  readonly render: OAuthCallbackPageRenderer;
+  readonly render: OAuthCallbackPageRenderer | undefined;
+  /**
+   * Notified exactly once when the browser callback fires and its status
+   * (success/error) is known. Lets the flow react immediately instead of
+   * waiting on pi-ai (which hangs on non-success callbacks).
+   */
+  readonly onResult?: ((status: OAuthCallbackPageStatus, context: OAuthCallbackPageContext) => void) | undefined;
 }
 
 type ServerResponseEnd = ServerResponse['end'];
@@ -267,30 +325,88 @@ const OAUTH_CALLBACK_ROUTES: Record<string, OAuthCallbackRoute> = {
 };
 
 let activeOAuthCallbackPageShim: ActiveOAuthCallbackPageShim | null = null;
+/** Ensures `onResult` fires at most once per installed shim. */
+let oauthCallbackResultNotified = false;
+
+/** Default overall OAuth flow timeout (pi-ai hangs without this). */
+const DEFAULT_OAUTH_FLOW_TIMEOUT_MS = 5 * 60_000;
+
+/**
+ * Probe whether something is already listening on a loopback port. Used to
+ * fail an OAuth flow fast (before opening a browser) when the provider's
+ * fixed callback port is occupied — otherwise pi-ai binds the other stack /
+ * the browser hits the wrong listener and the user gets a dead page while
+ * pi-ai waits forever.
+ */
+function probeCallbackPortInUse(port: number, host: string): Promise<boolean> {
+  const net = nodeRequire('node:net') as typeof import('node:net');
+  return new Promise((resolve) => {
+    let settled = false;
+    const finish = (inUse: boolean) => {
+      if (settled) return;
+      settled = true;
+      socket.destroy();
+      resolve(inUse);
+    };
+    const socket = net.connect({ port, host });
+    socket.once('connect', () => finish(true));
+    socket.once('error', () => finish(false));
+    socket.setTimeout(600, () => finish(false));
+  });
+}
+
+/**
+ * Throw an `OAuthError('callback_port_in_use')` if the provider's fixed
+ * callback port is occupied on either IPv4 or IPv6 loopback. No-op for
+ * providers without a known callback route (manual/device-code flows).
+ */
+async function assertOAuthCallbackPortAvailable(provider: string): Promise<void> {
+  const route = OAUTH_CALLBACK_ROUTES[provider];
+  if (!route) return;
+
+  for (const host of ['127.0.0.1', '::1']) {
+    if (await probeCallbackPortInUse(route.port, host)) {
+      throw new OAuthError(
+        'callback_port_in_use',
+        provider,
+        `OAuth callback port ${route.port} for "${provider}" is already in use ` +
+        `(detected on ${host}). This is a fixed port: another application is ` +
+        `holding it, or a previous sign-in did not finish. Close that ` +
+        `application (or restart the host process), then try again.`,
+        { port: route.port },
+      );
+    }
+  }
+}
 
-async function withOAuthCallbackPageShim<T>(
+/**
+ * Install the callback-page shim for a flow when there is a known callback
+ * route AND something to do with it (a custom renderer and/or a result
+ * observer). Returns a release function (a no-op when no shim was installed).
+ *
+ * Unlike a `try/finally` wrapper around pi-ai's `login()`, the caller owns
+ * the release lifecycle: pi-ai's callback-server flows hang forever on a
+ * non-success callback, so cleanup must be tied to the flow's own
+ * race/timeout, not to awaiting the (possibly never-settling) login promise.
+ */
+function maybeInstallOAuthCallbackShim(
   provider: string,
   providerName: string,
   render: OAuthCallbackPageRenderer | undefined,
-  run: () => Promise<T>,
-): Promise<T> {
+  onResult: ActiveOAuthCallbackPageShim['onResult'],
+): () => void {
   const route = OAUTH_CALLBACK_ROUTES[provider];
-  if (!render || !route) {
-    return run();
+  if (!route || (!render && !onResult)) {
+    return () => {};
   }
 
-  const release = installOAuthCallbackPageShim({
+  return installOAuthCallbackPageShim({
     provider,
     providerName,
     route,
     render,
+    onResult,
   });
-
-  try {
-    return await run();
-  } finally {
-    release();
-  }
 }
 
 function installOAuthCallbackPageShim(shim: ActiveOAuthCallbackPageShim): () => void {
@@ -304,6 +420,7 @@ function installOAuthCallbackPageShim(shim: ActiveOAuthCallbackPageShim): () =>
   const prototype = http.ServerResponse.prototype;
   const previousEnd = prototype.end;
   activeOAuthCallbackPageShim = shim;
+  oauthCallbackResultNotified = false;
 
   const patchedEnd = function patchedOAuthCallbackEnd(this: ServerResponse, ...args: unknown[]) {
     const replacement = maybeRenderOAuthCallbackPage(this, args[0]);
@@ -374,6 +491,19 @@ function maybeRenderOAuthCallbackPage(response: ServerResponse, chunk: unknown):
     context.details = details;
   }
 
+  // Notify the flow that the browser callback fired (once). This lets
+  // initiateOAuth react to a failed callback immediately rather than
+  // waiting on pi-ai, which hangs on non-success callbacks.
+  if (!oauthCallbackResultNotified && shim.onResult) {
+    oauthCallbackResultNotified = true;
+    try {
+      shim.onResult(status, context);
+    } catch {
+      // An observer must never break the callback response.
+    }
+  }
+
+  if (!shim.render) return null;
   try {
     const rendered = shim.render(context);
     return typeof rendered === 'string' && rendered.trim().length > 0 ? rendered : null;
@@ -732,41 +862,112 @@ export class ProviderManager implements IProviderManager {
    * @param provider - OAuth provider identifier
    * @param callbacks - UI callbacks for auth URL, prompts, and progress
    * @returns The OAuth credentials and display metadata
-   * @throws Error if the provider does not support OAuth or pi-ai is not installed
+   * @throws {OAuthError} `unsupported_provider`, `callback_port_in_use`,
+   *   `cancelled`, `timed_out`, or `callback_failed`. Other errors (e.g.
+   *   network/token-exchange failures from pi-ai) propagate as-is.
    */
   async initiateOAuth(provider: string, callbacks: OAuthCallbacks): Promise<OAuthResult> {
     const oauthModule = await loadPiAiOAuth();
     const oauthProvider = oauthModule.getOAuthProvider?.(provider);
     if (!oauthProvider) {
-      throw new Error(`Provider "${provider}" does not support OAuth`);
+      throw new OAuthError(
+        'unsupported_provider',
+        provider,
+        `Provider "${provider}" does not support OAuth`,
+      );
     }
 
-    this.activeOAuthAbort = new AbortController();
+    // (A) Fail fast — before opening a browser — if the provider's fixed
+    // callback port is already taken. Otherwise pi-ai binds the other
+    // stack, the browser hits the wrong listener, and pi-ai waits forever.
+    await assertOAuthCallbackPortAvailable(provider);
 
-    try {
-      const rawCredentials = await withOAuthCallbackPageShim(
+    const abort = new AbortController();
+    this.activeOAuthAbort = abort;
+
+    // (C) pi-ai only settles its callback wait on success; on a failed
+    // callback (e.g. state mismatch) it hangs. The render shim already sees
+    // that response — use it to fail the flow immediately with the reason.
+    let failFromCallback!: (err: OAuthError) => void;
+    const callbackFailure = new Promise<never>((_, reject) => {
+      failFromCallback = reject;
+    });
+    const handleCallbackResult = (
+      status: OAuthCallbackPageStatus,
+      ctx: OAuthCallbackPageContext,
+    ): void => {
+      if (status !== 'error') return;
+      const detail = ctx.details ? ` (${ctx.details})` : '';
+      failFromCallback(new OAuthError(
+        'callback_failed',
         provider,
-        oauthProvider.name,
-        callbacks.renderCallbackPage,
-        () => oauthProvider.login({
-          onAuth: callbacks.onAuth,
-          onPrompt: callbacks.onPrompt,
-          onProgress: callbacks.onProgress,
-          onManualCodeInput: callbacks.onManualCodeInput,
-          onSelect: callbacks.onSelect,
-          signal: this.activeOAuthAbort!.signal,
-        }),
-      );
+        `OAuth callback for "${provider}" reported a failure: ${ctx.message}${detail}`,
+      ));
+    };
 
-      this.activeOAuthAbort = null;
+    const releaseShim = maybeInstallOAuthCallbackShim(
+      provider,
+      oauthProvider.name,
+      callbacks.renderCallbackPage,
+      handleCallbackResult,
+    );
+
+    // (B) pi-ai callback servers ignore the abort signal, so cancellation
+    // and timeout are enforced here. Without this the flow hangs forever.
+    const timeoutMs = callbacks.timeoutMs ?? DEFAULT_OAUTH_FLOW_TIMEOUT_MS;
+    let timer: ReturnType<typeof setTimeout> | undefined;
+    const timeout = new Promise<never>((_, reject) => {
+      if (timeoutMs > 0 && Number.isFinite(timeoutMs)) {
+        timer = setTimeout(() => reject(new OAuthError(
+          'timed_out',
+          provider,
+          `OAuth flow for "${provider}" timed out after ${timeoutMs}ms.`,
+        )), timeoutMs);
+        timer.unref?.();
+      }
+    });
+    const cancelled = new Promise<never>((_, reject) => {
+      abort.signal.addEventListener('abort', () => reject(new OAuthError(
+        'cancelled',
+        provider,
+        `OAuth flow for "${provider}" was cancelled.`,
+      )), { once: true });
+    });
+
+    const login = oauthProvider.login({
+      onAuth: callbacks.onAuth,
+      onPrompt: callbacks.onPrompt,
+      onProgress: callbacks.onProgress,
+      onManualCodeInput: callbacks.onManualCodeInput,
+      onSelect: callbacks.onSelect,
+      signal: abort.signal,
+    }) as Promise<Record<string, unknown>>;
+    // Whichever promise loses the race may still settle later (pi-ai's
+    // login can hang or settle late; the aux promises can reject after the
+    // race is decided). Attach inert handlers so a late rejection never
+    // surfaces as an unhandled rejection. Promise.race still observes the
+    // first settlement independently.
+    login.catch(() => {});
+    cancelled.catch(() => {});
+    timeout.catch(() => {});
+    callbackFailure.catch(() => {});
+
+    try {
+      const rawCredentials = await Promise.race([
+        login,
+        cancelled,
+        timeout,
+        callbackFailure,
+      ]);
 
       const credentials = JSON.stringify(rawCredentials);
       const meta = buildOAuthMeta(provider, rawCredentials);
 
       return { credentials, meta };
-    } catch (err) {
-      this.activeOAuthAbort = null;
-      throw err;
+    } finally {
+      if (timer) clearTimeout(timer);
+      releaseShim();
+      if (this.activeOAuthAbort === abort) this.activeOAuthAbort = null;
     }
   }