fix: clean up interrupted session state on restart

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

src/main/AryxAppService.ts

@@ -156,6 +156,11 @@ function isSidecarStoppedBeforeCompletionError(error: unknown): error is Error {
   return error instanceof Error && error.message === SIDECAR_STOPPED_BEFORE_COMPLETION_MESSAGE;
 }
 
+const INTERRUPTED_RUN_ERROR =
+  'This session was interrupted because Aryx restarted while a run was in progress.';
+const INTERRUPTED_APPROVAL_ERROR =
+  'Pending approval was interrupted because Aryx restarted before a decision was recorded.';
+
 export class AryxAppService extends EventEmitter<AppServiceEvents> {
   private readonly workspaceRepository = new WorkspaceRepository();
   private readonly sidecar = new SidecarClient();
@@ -195,7 +200,7 @@ export class AryxAppService extends EventEmitter<AppServiceEvents> {
         || didSyncProjectTooling
         || didPruneSelections
         || didPruneApprovalTools
-        || this.failInterruptedPendingApprovals(this.workspace)
+        || this.cleanupInterruptedSessions(this.workspace)
       ) {
         await this.workspaceRepository.save(this.workspace);
       }
@@ -2015,33 +2020,41 @@ export class AryxAppService extends EventEmitter<AppServiceEvents> {
     this.emit('session-event', event);
   }
 
-  private failInterruptedPendingApprovals(workspace: WorkspaceState): boolean {
+  private cleanupInterruptedSessions(workspace: WorkspaceState): boolean {
     let changed = false;
 
     for (const session of workspace.sessions) {
       const pendingApprovals = listPendingApprovals(session);
-      if (pendingApprovals.length === 0) {
+      const hasPendingUserInput = session.pendingUserInput !== undefined;
+      const failedRequestIds = new Set(
+        session.runs
+          .filter((run) => run.status === 'running')
+          .map((run) => run.requestId),
+      );
+      if (pendingApprovals.length === 0 && !hasPendingUserInput && failedRequestIds.size === 0) {
         continue;
       }
 
       changed = true;
       const failedAt = nowIso();
-      const error = 'Pending approval was interrupted because Aryx restarted before a decision was recorded.';
+      if (pendingApprovals.length > 0) {
-      const requestIds = this.rejectPendingApprovals(session, failedAt, error);
+        for (const requestId of this.rejectPendingApprovals(session, failedAt, INTERRUPTED_APPROVAL_ERROR)) {
-      session.status = 'error';
+          failedRequestIds.add(requestId);
-      session.lastError = error;
-      session.updatedAt = failedAt;
-
-      if (requestIds.length === 0) {
-        const fallbackRequestId = session.runs.find((run) => run.status === 'running')?.requestId;
-        if (fallbackRequestId) {
-          requestIds.push(fallbackRequestId);
         }
       }
 
-      for (const requestId of requestIds) {
+      if (session.pendingUserInput) {
+        this.pendingUserInputHandles.delete(session.pendingUserInput.id);
+        session.pendingUserInput = undefined;
+      }
+
+      session.status = 'error';
+      session.lastError = INTERRUPTED_RUN_ERROR;
+      session.updatedAt = failedAt;
+
+      for (const requestId of failedRequestIds) {
         this.updateSessionRun(session, requestId, (run) =>
-          failSessionRunRecord(run, failedAt, error));
+          failSessionRunRecord(run, failedAt, INTERRUPTED_RUN_ERROR));
       }
     }
 

tests/main/appServiceInterruptedSessions.test.ts

@@ -0,0 +1,260 @@
+import { describe, expect, mock, test } from 'bun:test';
+
+import type { PendingApprovalRecord } from '@shared/domain/approval';
+import type { PendingMcpAuthRecord } from '@shared/domain/mcpAuth';
+import type { PatternDefinition } from '@shared/domain/pattern';
+import type { PendingPlanReviewRecord } from '@shared/domain/planReview';
+import type { SessionRunRecord } from '@shared/domain/runTimeline';
+import type { SessionRecord } from '@shared/domain/session';
+import type { PendingUserInputRecord } from '@shared/domain/userInput';
+import { createWorkspaceSeed, type WorkspaceState } from '@shared/domain/workspace';
+
+const TIMESTAMP = '2026-03-28T00:00:00.000Z';
+const INTERRUPTED_RUN_ERROR =
+  'This session was interrupted because Aryx restarted while a run was in progress.';
+
+mock.module('electron', () => {
+  const electronMock = {
+    app: {
+      isPackaged: false,
+      getAppPath: () => 'C:\\workspace\\personal\\repositories\\aryx',
+      getPath: () => 'C:\\workspace\\personal\\repositories\\aryx\\tests\\fixtures',
+    },
+    dialog: {
+      showOpenDialog: async () => ({ canceled: true, filePaths: [] }),
+    },
+    shell: {
+      openPath: async () => '',
+    },
+  };
+
+  return {
+    ...electronMock,
+    default: electronMock,
+  };
+});
+
+mock.module('keytar', () => ({
+  default: {
+    getPassword: async () => null,
+    setPassword: async () => undefined,
+    deletePassword: async () => false,
+  },
+}));
+
+const { AryxAppService } = await import('@main/AryxAppService');
+
+function requireSinglePattern(workspace: WorkspaceState): PatternDefinition {
+  const pattern = workspace.patterns.find((candidate) => candidate.mode === 'single');
+  if (!pattern) {
+    throw new Error('Expected the workspace seed to include a single-agent pattern.');
+  }
+
+  return pattern;
+}
+
+function createSession(patternId: string, overrides?: Partial<SessionRecord>): SessionRecord {
+  return {
+    id: 'session-1',
+    projectId: 'project-1',
+    patternId,
+    title: 'Session',
+    createdAt: TIMESTAMP,
+    updatedAt: TIMESTAMP,
+    status: 'idle',
+    messages: [],
+    runs: [],
+    ...overrides,
+  };
+}
+
+function createRun(
+  pattern: PatternDefinition,
+  overrides?: Partial<SessionRunRecord>,
+): SessionRunRecord {
+  return {
+    id: 'run-1',
+    requestId: 'request-1',
+    projectId: 'project-1',
+    projectPath: 'C:\\workspace\\personal\\repositories\\aryx',
+    workspaceKind: 'project',
+    patternId: pattern.id,
+    patternName: pattern.name,
+    patternMode: pattern.mode,
+    triggerMessageId: 'message-1',
+    startedAt: TIMESTAMP,
+    status: 'running',
+    agents: [],
+    events: [
+      {
+        id: 'run-event-1',
+        kind: 'run-started',
+        occurredAt: TIMESTAMP,
+        status: 'completed',
+      },
+    ],
+    ...overrides,
+  };
+}
+
+function createPendingApproval(id: string, title: string): PendingApprovalRecord {
+  return {
+    id,
+    kind: 'tool-call',
+    status: 'pending',
+    requestedAt: TIMESTAMP,
+    title,
+  };
+}
+
+function createPendingUserInput(overrides?: Partial<PendingUserInputRecord>): PendingUserInputRecord {
+  return {
+    id: 'user-input-1',
+    status: 'pending',
+    question: 'What should I do next?',
+    allowFreeform: true,
+    requestedAt: TIMESTAMP,
+    ...overrides,
+  };
+}
+
+function createPendingPlanReview(overrides?: Partial<PendingPlanReviewRecord>): PendingPlanReviewRecord {
+  return {
+    id: 'plan-review-1',
+    status: 'pending',
+    summary: 'Review the plan before continuing.',
+    planContent: '1. Investigate\n2. Implement',
+    requestedAt: TIMESTAMP,
+    ...overrides,
+  };
+}
+
+function createPendingMcpAuth(overrides?: Partial<PendingMcpAuthRecord>): PendingMcpAuthRecord {
+  return {
+    id: 'oauth-1',
+    status: 'pending',
+    serverName: 'Example MCP',
+    serverUrl: 'https://example.com/mcp',
+    requestedAt: TIMESTAMP,
+    ...overrides,
+  };
+}
+
+function createService(
+  workspace: WorkspaceState,
+): {
+  service: InstanceType<typeof AryxAppService>;
+  getSaveCalls: () => number;
+} {
+  let saveCalls = 0;
+  const service = new AryxAppService();
+  const internals = service as unknown as Record<string, unknown>;
+
+  internals.workspaceRepository = {
+    load: async () => workspace,
+    save: async () => {
+      saveCalls += 1;
+    },
+  };
+  internals.syncUserDiscoveredTooling = async () => false;
+  internals.syncProjectDiscoveredTooling = async () => false;
+  internals.pruneUnavailableSessionToolingSelections = () => false;
+  internals.pruneUnavailableApprovalTools = async () => false;
+  internals.refreshProjectGitContext = async () => undefined;
+
+  return {
+    service,
+    getSaveCalls: () => saveCalls,
+  };
+}
+
+describe('AryxAppService interrupted session cleanup', () => {
+  test('clears stale approvals and user input, then fails the interrupted run on load', async () => {
+    const workspace = createWorkspaceSeed();
+    const pattern = requireSinglePattern(workspace);
+    const runningRun = createRun(pattern);
+    const session = createSession(pattern.id, {
+      status: 'running',
+      pendingApproval: createPendingApproval('approval-1', 'Approve reading the repo'),
+      pendingApprovalQueue: [createPendingApproval('approval-2', 'Approve writing the repo')],
+      pendingUserInput: createPendingUserInput(),
+      runs: [runningRun],
+    });
+    workspace.sessions = [session];
+
+    const { service, getSaveCalls } = createService(workspace);
+
+    const loaded = await service.loadWorkspace();
+    const cleanedSession = loaded.sessions[0];
+    if (!cleanedSession) {
+      throw new Error('Expected loadWorkspace to return the interrupted session.');
+    }
+
+    expect(cleanedSession.pendingApproval).toBeUndefined();
+    expect(cleanedSession.pendingApprovalQueue).toBeUndefined();
+    expect(cleanedSession.pendingUserInput).toBeUndefined();
+    expect(cleanedSession.status).toBe('error');
+    expect(cleanedSession.lastError).toBe(INTERRUPTED_RUN_ERROR);
+    expect(getSaveCalls()).toBe(1);
+
+    const failedRun = cleanedSession.runs[0];
+    if (!failedRun) {
+      throw new Error('Expected the interrupted run to remain attached to the session.');
+    }
+
+    expect(failedRun.status).toBe('error');
+    expect(failedRun.completedAt).toBe(cleanedSession.updatedAt);
+    expect(failedRun.events.some((event) => event.kind === 'run-failed' && event.error === INTERRUPTED_RUN_ERROR))
+      .toBe(true);
+    expect(failedRun.events.filter((event) => event.kind === 'approval').map((event) => event.decision))
+      .toEqual(['rejected', 'rejected']);
+  });
+
+  test('fails sessions that were left in running state even without pending interaction records', async () => {
+    const workspace = createWorkspaceSeed();
+    const pattern = requireSinglePattern(workspace);
+    const session = createSession(pattern.id, {
+      status: 'running',
+      runs: [createRun(pattern)],
+    });
+    workspace.sessions = [session];
+
+    const { service, getSaveCalls } = createService(workspace);
+
+    const loaded = await service.loadWorkspace();
+    const cleanedSession = loaded.sessions[0];
+    if (!cleanedSession) {
+      throw new Error('Expected loadWorkspace to return the running session.');
+    }
+
+    expect(cleanedSession.status).toBe('error');
+    expect(cleanedSession.lastError).toBe(INTERRUPTED_RUN_ERROR);
+    expect(cleanedSession.runs[0]?.status).toBe('error');
+    expect(getSaveCalls()).toBe(1);
+  });
+
+  test('preserves restart-safe plan review and MCP auth prompts', async () => {
+    const workspace = createWorkspaceSeed();
+    const pattern = requireSinglePattern(workspace);
+    const planReview = createPendingPlanReview();
+    const mcpAuth = createPendingMcpAuth();
+    const session = createSession(pattern.id, {
+      pendingPlanReview: planReview,
+      pendingMcpAuth: mcpAuth,
+    });
+    workspace.sessions = [session];
+
+    const { service, getSaveCalls } = createService(workspace);
+
+    const loaded = await service.loadWorkspace();
+    const cleanedSession = loaded.sessions[0];
+    if (!cleanedSession) {
+      throw new Error('Expected loadWorkspace to return the session.');
+    }
+
+    expect(cleanedSession.status).toBe('idle');
+    expect(cleanedSession.pendingPlanReview).toEqual(planReview);
+    expect(cleanedSession.pendingMcpAuth).toEqual(mcpAuth);
+    expect(getSaveCalls()).toBe(0);
+  });
+});