fix(realtime): isolate notification failures

src/server/sessions/authService.test.ts

@@ -5,7 +5,7 @@ import { ModelRuntime } from "@earendil-works/pi-coding-agent";
 import { InMemoryCredentialStore, type AuthPrompt, type Credential } from "@earendil-works/pi-ai";
 import { afterEach, describe, expect, it, vi } from "vitest";
 import type { OAuthFlowState } from "../../shared/apiTypes.js";
-import { AuthService, type AuthChange } from "./authService.js";
+import { AuthService, type AuthChange, type AuthServiceLogger } from "./authService.js";
 import { OAuthLoginFlowService } from "./oauthLoginFlowService.js";
 
 const tempDirs: string[] = [];
@@ -41,6 +41,54 @@ describe("AuthService", () => {
     auth.dispose();
   });
 
+  it("persists an API key and attempts every listener when propagation fails", async () => {
+    const error = vi.fn();
+    const logger: AuthServiceLogger = { error };
+    const { auth, credentials, changes } = await createAuthService({}, logger);
+    const failure = new Error("session auth refresh failed");
+    const attempts: string[] = [];
+    auth.subscribe(() => {
+      attempts.push("throwing");
+      throw failure;
+    });
+    auth.subscribe(async () => {
+      await Promise.resolve();
+      attempts.push("healthy");
+    });
+
+    await expect(auth.saveApiKey("anthropic", "sk-test")).resolves.toEqual({ accepted: true });
+
+    await expect(credentials.read("anthropic")).resolves.toEqual({ type: "api_key", key: "sk-test" });
+    expect(changes).toEqual([{}]);
+    expect(attempts).toEqual(["throwing", "healthy"]);
+    expect(error).toHaveBeenCalledWith(
+      { err: failure, operation: "login", providerId: "anthropic", authType: "api_key" },
+      "auth-change listener failed",
+    );
+    auth.dispose();
+  });
+
+  it("removes a credential when auth-change propagation rejects", async () => {
+    const error = vi.fn();
+    const logger: AuthServiceLogger = { error };
+    const { auth, credentials, changes } = await createAuthService(
+      { anthropic: { type: "api_key", key: "sk-test" } },
+      logger,
+    );
+    const failure = new Error("session logout refresh failed");
+    auth.subscribe(() => Promise.reject(failure));
+
+    await expect(auth.logoutProvider("anthropic")).resolves.toEqual({ accepted: true });
+
+    await expect(credentials.read("anthropic")).resolves.toBeUndefined();
+    expect(changes).toEqual([{ removedProviderId: "anthropic" }]);
+    expect(error).toHaveBeenCalledWith(
+      { err: failure, operation: "logout", providerId: "anthropic" },
+      "auth-change listener failed",
+    );
+    auth.dispose();
+  });
+
   it("rejects blank API keys", async () => {
     const { auth, changes } = await createAuthService();
 
@@ -236,22 +284,48 @@ describe("AuthService", () => {
 
     refresh.mockClear();
     if (startOptions.onComplete === undefined) throw new Error("Expected OAuth completion callback");
-    startOptions.onComplete();
-    await vi.waitFor(() => { expect(changes).toEqual([{}]); });
+    await startOptions.onComplete();
+    expect(changes).toEqual([{}]);
 
     expect(refresh).not.toHaveBeenCalled();
     auth.dispose();
     expect(authFlows.disposed).toBe(true);
   });
+
+  it("completes OAuth when an auth-change listener rejects", async () => {
+    const error = vi.fn();
+    const logger: AuthServiceLogger = { error };
+    const { auth, runtime, changes } = await createAuthService({}, logger);
+    const provider = runtime.getProviders().find((option) => option.id === "anthropic" && option.auth.oauth !== undefined);
+    if (provider === undefined) throw new Error("Expected built-in OAuth provider");
+    vi.spyOn(runtime, "login").mockResolvedValue({
+      type: "oauth",
+      refresh: "refresh-token",
+      access: "access-token",
+      expires: Date.now() + 60_000,
+    });
+    const failure = new Error("session OAuth refresh failed");
+    auth.subscribe(() => Promise.reject(failure));
+
+    const state = await auth.startOAuthLogin(provider.id);
+    await vi.waitFor(() => { expect(auth.oauthFlow(state.flowId).status).toBe("complete"); });
+
+    expect(changes).toEqual([{}]);
+    expect(error).toHaveBeenCalledWith(
+      { err: failure, operation: "login", providerId: provider.id, authType: "oauth" },
+      "auth-change listener failed",
+    );
+    auth.dispose();
+  });
 });
 
-async function createAuthService(seed: Record<string, Credential> = {}) {
+async function createAuthService(seed: Record<string, Credential> = {}, logger?: AuthServiceLogger) {
   const credentials = new InMemoryCredentialStore();
   for (const [providerId, credential] of Object.entries(seed)) {
     await credentials.modify(providerId, () => Promise.resolve(credential));
   }
   const runtime = await ModelRuntime.create({ credentials, modelsPath: null, allowModelNetwork: false });
-  const auth = await AuthService.create({ runtime });
+  const auth = await AuthService.create({ runtime, ...(logger === undefined ? {} : { logger }) });
   const changes: AuthChange[] = [];
   auth.subscribe((change) => { changes.push(change); });
   return { auth, runtime, credentials, changes };

src/server/sessions/authService.ts

@@ -9,14 +9,28 @@ export interface AuthChange {
   removedProviderId?: string;
 }
 
-type AuthChangeListener = (change: AuthChange) => void;
+type AuthChangeListener = (change: AuthChange) => void | Promise<void>;
 
 export interface AuthServiceDependencies {
   agentDir?: string;
   runtime?: ModelRuntime;
   authFlows?: OAuthLoginFlowService;
+  logger?: AuthServiceLogger;
 }
 
+/** Minimal structured-logging seam for non-fatal auth propagation failures. */
+export interface AuthServiceLogger {
+  error(details: Record<string, unknown>, message: string): void;
+}
+
+interface AuthChangeContext {
+  operation: "login" | "logout";
+  providerId: string;
+  authType?: AuthType;
+}
+
+const noopLogger: AuthServiceLogger = { error() { /* no-op */ } };
+
 export function createModelRuntimeForAgentDir(agentDir: string): Promise<ModelRuntime> {
   return ModelRuntime.create({ authPath: join(agentDir, "auth.json"), modelsPath: join(agentDir, "models.json") });
 }
@@ -24,17 +38,19 @@ export function createModelRuntimeForAgentDir(agentDir: string): Promise<ModelRu
 export class AuthService {
   readonly runtime: ModelRuntime;
   private readonly authFlows: OAuthLoginFlowService;
+  private readonly logger: AuthServiceLogger;
   private readonly listeners = new Set<AuthChangeListener>();
 
-  private constructor(runtime: ModelRuntime, authFlows: OAuthLoginFlowService) {
+  private constructor(runtime: ModelRuntime, authFlows: OAuthLoginFlowService, logger: AuthServiceLogger) {
     this.runtime = runtime;
     this.authFlows = authFlows;
+    this.logger = logger;
   }
 
   static async create(deps: AuthServiceDependencies = {}): Promise<AuthService> {
     const runtime = deps.runtime ?? (deps.agentDir === undefined ? await ModelRuntime.create({}) : await createModelRuntimeForAgentDir(deps.agentDir));
     const authFlows = deps.authFlows ?? new OAuthLoginFlowService();
-    return new AuthService(runtime, authFlows);
+    return new AuthService(runtime, authFlows, deps.logger ?? noopLogger);
   }
 
   subscribe(listener: AuthChangeListener): () => void {
@@ -74,13 +90,13 @@ export class AuthService {
       notify: () => undefined,
     };
     await this.runtime.login(providerId, "api_key", interaction);
-    this.emit({});
+    await this.emit({}, { operation: "login", providerId, authType: "api_key" });
     return { accepted: true };
   }
 
   async logoutProvider(providerId: string): Promise<{ accepted: true }> {
     await this.runtime.logout(providerId);
-    this.emit({ removedProviderId: providerId });
+    await this.emit({ removedProviderId: providerId }, { operation: "logout", providerId });
     return { accepted: true };
   }
 
@@ -90,9 +106,7 @@ export class AuthService {
       providerId,
       providerName: provider.name,
       runtime: this.runtime,
-      onComplete: () => {
-        this.emit({});
-      },
+      onComplete: () => this.emit({}, { operation: "login", providerId, authType: "oauth" }),
     });
   }
 
@@ -108,8 +122,13 @@ export class AuthService {
     return this.authFlows.cancel(flowId);
   }
 
-  private emit(change: AuthChange): void {
-    for (const listener of this.listeners) listener(change);
+  private async emit(change: AuthChange, context: AuthChangeContext): Promise<void> {
+    const results = await Promise.allSettled([...this.listeners].map(async (listener) => listener(change)));
+    for (const result of results) {
+      if (result.status === "rejected") {
+        this.logger.error({ err: result.reason, ...context }, "auth-change listener failed");
+      }
+    }
   }
 
   private async requireApiKeyLoginProvider(providerId: string) {

src/server/sessions/oauthLoginFlowService.test.ts

@@ -41,6 +41,25 @@ describe("OAuthLoginFlowService", () => {
     service.dispose();
   });
 
+  it("awaits async completion propagation before marking the flow complete", async () => {
+    const completion = deferred<undefined>();
+    const service = new OAuthLoginFlowService();
+    const state = service.start({
+      providerId: "test-provider",
+      providerName: "Test Provider",
+      runtime: fakeRuntime(() => Promise.resolve()),
+      onComplete: () => completion.promise,
+    });
+
+    await flushAsyncLogin();
+    expect(service.get(state.flowId).status).toBe("running");
+
+    completion.resolve(undefined);
+    await flushAsyncLogin();
+    expect(service.get(state.flowId).status).toBe("complete");
+    service.dispose();
+  });
+
   it("allows blank text responses for providers that use blank as a default", async () => {
     let domain: string | undefined;
     const service = new OAuthLoginFlowService();

src/server/sessions/oauthLoginFlowService.ts

@@ -52,7 +52,7 @@ export class OAuthLoginFlowService {
     providerId: string;
     providerName: string;
     runtime: OAuthLoginRuntime;
-    onComplete?: () => void;
+    onComplete?: () => void | Promise<void>;
   }): OAuthFlowState {
     const flowId = crypto.randomUUID();
     const abort = new AbortController();
@@ -81,11 +81,12 @@ export class OAuthLoginFlowService {
     };
 
     void options.runtime.login(options.providerId, "oauth", interaction)
-      .then(() => {
+      .then(async () => {
         if (!this.isCurrentRunning(record)) return;
         this.clearPending(record);
+        await options.onComplete?.();
+        if (!this.isCurrentRunning(record)) return;
         this.markTerminal(record, { ...withoutInteraction(record.state), status: "complete", progress: [...record.state.progress, "Login complete"] });
-        options.onComplete?.();
       })
       .catch((error: unknown) => {
         if (this.flows.get(record.flowId) !== record) return;