fix(assistant): a change left waiting past its day no longer holds the next one back

The open changes of a thread are now the ones still inside their decision
window. A call older than a day already reads as expired in the thread and
can no longer be decided, but it stayed approval_requested until the nightly
sweep, so "+ Tour", "+ Day" and "Plan this" answered decide_first with
nothing left to decide, and a decision had to name the expired call too.
listOpen takes the window's start, and every caller passes the same cutoff.

server/src/db/repositories/AssistantToolCalls.repository.ts

@@ -145,13 +145,18 @@ export class AssistantToolCallsRepository extends TrekRepository<AssistantToolCa
       .execute();
   }
 
-  /** The calls of a thread still waiting for a decision. */
-  async listOpen(threadId: number): Promise<AssistantToolCallRow[]> {
+  /**
+   * The calls of a thread still waiting for a decision, proposed at or after
+   * `notBefore`: an older one has expired, as the thread shows it and as
+   * `claimDecision` refuses it, even before the nightly sweep marks it so.
+   */
+  async listOpen(threadId: number, notBefore: string): Promise<AssistantToolCallRow[]> {
     return this.db()
       .selectFrom('assistant_tool_calls')
       .select(COLUMNS)
       .where('thread_id', '=', threadId)
       .where('state', '=', 'approval_requested')
+      .where('created_at', '>=', notBefore)
       .orderBy('created_at')
       .orderBy('id')
       .execute();

server/src/nest/assistant/assistant-found-places.service.ts

@@ -30,7 +30,7 @@ import {
 } from './assistant-context';
 import { partsOf, toThreadMessages } from './assistant-history';
 import { AssistantStreamRegistry } from './assistant-stream.registry';
-import { ADD_FOUND_PLACE_TOOL, TURNS_PER_MINUTE } from './assistant-tools.constants';
+import { ADD_FOUND_PLACE_TOOL, decisionCutoff, TURNS_PER_MINUTE } from './assistant-tools.constants';
 import { AssistantToolsService } from './assistant-tools.service';
 import { AssistantCardContext } from './cards/card-context';
 import { recordOf } from './cards/card-values';
@@ -248,7 +248,7 @@ export class AssistantFoundPlacesService {
     tourId: number | null,
     argsOf: ArgsOf,
   ): Promise<void> {
-    if ((await this.toolCalls.listOpen(threadId)).length > 0) {
+    if ((await this.toolCalls.listOpen(threadId, decisionCutoff())).length > 0) {
       throw aiRefusal('decide_first', 'Decide on the changes that are waiting first');
     }
     const place = foundPlace(await this.messages.listLatest(threadId, SEARCHED_ROWS), req.ref);

server/src/nest/assistant/assistant-proposals.service.ts

@@ -25,7 +25,7 @@ import { partsOf, toThreadMessages } from './assistant-history';
 import { isSportPlan, SPORT_CREATES, sportTakeArgsOf, tourTypeWord } from './assistant-proposal-sports';
 import { isWayProposal, WAY_CREATES, wayTakeArgsOf } from './assistant-proposal-ways';
 import { AssistantStreamRegistry } from './assistant-stream.registry';
-import { TAKE_PROPOSAL_TOOL, TURNS_PER_MINUTE } from './assistant-tools.constants';
+import { decisionCutoff, TAKE_PROPOSAL_TOOL, TURNS_PER_MINUTE } from './assistant-tools.constants';
 import { AssistantToolsService, type ToolRun } from './assistant-tools.service';
 import { AssistantCardContext } from './cards/card-context';
 import { recordOf, type Row } from './cards/card-values';
@@ -276,7 +276,7 @@ export class AssistantProposalsService {
   }
 
   private async hold(userId: number, tripId: number, threadId: number, req: AssistantTakeProposalRequest) {
-    if ((await this.toolCalls.listOpen(threadId)).length > 0) {
+    if ((await this.toolCalls.listOpen(threadId, decisionCutoff())).length > 0) {
       throw aiRefusal('decide_first', 'Decide on the changes that are waiting first');
     }
     const stored = storedProposal(await this.messages.listLatest(threadId, SEARCHED_ROWS), req.toolCallId);

server/src/nest/assistant/assistant-retention.job.ts

@@ -7,7 +7,7 @@ import { AiConnectionsService } from '../ai-connections/ai-connections.service';
 import { AiUsageService } from '../ai-connections/ai-usage.service';
 import { logError, logInfo } from '../audit/audit-log.logger';
 import { CronRegistrarService } from '../scheduling/cron-registrar.service';
-import { APPROVAL_TTL_MS } from './assistant-tools.constants';
+import { decisionCutoff } from './assistant-tools.constants';
 import { InjectRepository } from '@mikro-orm/nestjs';
 import { Injectable, type OnApplicationBootstrap } from '@nestjs/common';
 
@@ -51,7 +51,7 @@ export class AssistantRetentionJob implements OnApplicationBootstrap {
           : 0;
       const orphaned = await this.threads.deleteWithoutAccess();
       if (idle + orphaned > 0) logInfo(`Assistant retention: removed ${idle + orphaned} conversation(s)`);
-      const expired = await this.toolCalls.expireBefore(dbNow(new Date(now.getTime() - APPROVAL_TTL_MS)));
+      const expired = await this.toolCalls.expireBefore(decisionCutoff(now));
       if (expired.length > 0) logInfo(`Assistant retention: ${expired.length} proposed change(s) expired`);
       await this.usage.purgeOlderThan(ASSISTANT_USAGE_RETENTION_DAYS);
     } catch (err: unknown) {

server/src/nest/assistant/assistant-tools.constants.ts

@@ -1,3 +1,4 @@
+import { dbNow, type DbTimestamp } from '../../db/types';
 import type { ToolUndo } from './cards/card-types';
 import { argId, idIn } from './cards/card-values';
 import type { AssistantApplied, AssistantChangeVerbKey } from '@trek/shared';
@@ -27,6 +28,11 @@ export const UNDO_WINDOW_MS = 15 * 60_000;
 /** How long a proposed change waits for a decision before it expires. */
 export const APPROVAL_TTL_MS = 24 * 60 * 60_000;
 
+/** The oldest a change still waiting at `now` may have been proposed and still be decided, as the database writes it. */
+export function decisionCutoff(now: Date = new Date()): DbTimestamp {
+  return dbNow(new Date(now.getTime() - APPROVAL_TTL_MS));
+}
+
 /** Turns (chat, decisions, undo) a user may start per minute. */
 export const TURNS_PER_MINUTE = 30;
 

server/src/nest/assistant/assistant.service.ts

@@ -45,8 +45,8 @@ import { AssistantScopes, findScopedCall, scopedThreads, tripScope } from './ass
 import { AssistantStreamRegistry } from './assistant-stream.registry';
 import { titleFrom } from './assistant-title';
 import {
-  APPROVAL_TTL_MS,
   ASSISTANT_SERVER_WRITE_TOOLS,
+  decisionCutoff,
   foundPlaceArgs,
   IMPORT_BOOKING_TOOL,
   REMEMBER_TOOL,
@@ -316,7 +316,7 @@ export class AssistantService {
   ): Promise<void> {
     if (!(await scopedThreads(this.threads, scope).find(threadId, userId))) throw threadNotFound();
     await this.admit(userId);
-    const open = await this.toolCalls.listOpen(threadId);
+    const open = await this.toolCalls.listOpen(threadId, decisionCutoff());
     if (open.length > 0 && open.every((call) => ASSISTANT_SERVER_WRITE_TOOLS[call.tool_name]?.quiet === true)) {
       await this.decideQuietly(userId, scope, threadId, req, channel);
       return;
@@ -624,7 +624,7 @@ export class AssistantService {
   }
 
   private async cancelOpen(threadId: number, now: string): Promise<void> {
-    const open = await this.toolCalls.listOpen(threadId);
+    const open = await this.toolCalls.listOpen(threadId, decisionCutoff());
     const claimed = await Promise.all(
       open.map((call) => this.toolCalls.claimDecision(call.id, threadId, false, dbNow(new Date(0)), now)),
     );
@@ -644,14 +644,16 @@ export class AssistantService {
 
   /**
    * Records the decisions, each only while its change still waits and is less
-   * than a day old. The request must name every waiting change and nothing
-   * else (422); when none could be taken any more, 409.
+   * than a day old. The request must name every change waiting within its day
+   * and nothing else (422); when none could be taken any more, 409.
    */
   private async claimDecisions(
     threadId: number,
     decisions: AssistantDecision[],
   ): Promise<Array<{ call: AssistantToolCallRow; approved: boolean }>> {
-    const open = await this.toolCalls.listOpen(threadId);
+    const now = new Date();
+    const notBefore = decisionCutoff(now);
+    const open = await this.toolCalls.listOpen(threadId, notBefore);
     if (open.length === 0) throw conflict('No change is waiting for a decision', { code: 'generic' });
     const wanted = new Map(decisions.map((decision) => [decision.toolCallId, decision.approved]));
     const complete =
@@ -659,8 +661,6 @@ export class AssistantService {
     if (!complete) {
       throw new DomainError(422, 'Decide on every change that is waiting', { details: { code: 'generic' } });
     }
-    const now = new Date();
-    const notBefore = dbNow(new Date(now.getTime() - APPROVAL_TTL_MS));
     // In the order the decisions name them, the order the chat shows the changes in: the changes of one step
     // share their time, and their ids sort at random, so only this order lets "undo all" walk them back.
     const position = new Map(decisions.map((decision, i) => [decision.toolCallId, i]));

server/tests/e2e/assistant.e2e.test.ts

@@ -27,6 +27,7 @@ import { DayAssignments } from '../../src/db/entities/DayAssignments.entity';
 import { Places } from '../../src/db/entities/Places.entity';
 import { Reservations } from '../../src/db/entities/Reservations.entity';
 import { Trips } from '../../src/db/entities/Trips.entity';
+import { dbNow } from '../../src/db/types';
 import { TURNS_PER_MINUTE } from '../../src/nest/assistant/assistant-tools.constants';
 import { AssistantToolsService } from '../../src/nest/assistant/assistant-tools.service';
 import { AssistantCardContext } from '../../src/nest/assistant/cards/card-context';
@@ -896,6 +897,43 @@ describe('Trip assistant e2e', () => {
     expect(provider.requests).toHaveLength(2);
   });
 
+  it('ASTE2E-025: a change left waiting past its day holds nothing back, and the next one is decided alone', async () => {
+    const t = await travelerWithTrip();
+    const [day] = await readTripDays(orm, t.tripId);
+    const { threadId } = await searchTurn(t);
+    const path = `${t.base}/threads/${threadId}/found-places`;
+    // The newest change the answer holds: a found place joins the answer of its search.
+    const changeOf = (res: { body: { message: { parts: AssistantMessagePart[] } } }) =>
+      res.body.message.parts
+        .flatMap((part) => (part.type === 'data-trek-change' ? [part.data.toolCallId] : []))
+        .at(-1) ?? '';
+    const stale = changeOf(await addFound(path, t.userId, { ref: 'call_find:0', dayId: day.id }));
+    // A day and an hour old: the thread shows it expired, and the nightly sweep has not run yet.
+    await updateRows(
+      orm,
+      AssistantToolCalls,
+      { id: stale },
+      { created_at: dbNow(new Date(Date.now() - 25 * 3_600_000)) },
+    );
+    const shown = await get(`${t.base}/threads/${threadId}`, t.userId);
+    const parts = (shown.body.messages as Array<{ parts: AssistantMessagePart[] }>).flatMap((m) => m.parts);
+    expect(parts.find((part) => part.type === 'tool-call' && part.toolCallId === stale)).toMatchObject({
+      approval: { resolution: 'expired' },
+    });
+
+    const next = await addFound(path, t.userId, { ref: 'call_find:1', dayId: day.id });
+    expect(next.status).toBe(200);
+    const fresh = changeOf(next);
+    expect(fresh).not.toBe(stale);
+    const decided = await post(`${t.base}/threads/${threadId}/decisions`, t.userId, {
+      ...CTX,
+      decisions: [{ toolCallId: fresh, approved: true }],
+    });
+    expect(decided.status).toBe(200);
+    expect(ofType(decided.chunks, 'data-trek-applied')[0].data).toMatchObject({ toolCallId: fresh });
+    expect((await findRow(orm, AssistantToolCalls, { id: stale }))?.state).toBe('approval_requested');
+  });
+
   it('ASTE2E-024: "+ Day" asks for the right to edit places: 403 and nothing held without it, 404 outside the trip', async () => {
     const t = await travelerWithTrip();
     const { user: member } = await makeUser(orm);

server/tests/unit/db/repositories/AssistantConversations.repository.test.ts

@@ -324,7 +324,9 @@ describe('proposed changes', () => {
     const { threadId, messageId } = await threadWithMessage();
     await calls.insertProposals([proposal('c1', threadId, messageId), proposal('c2', threadId, messageId)]);
     await calls.insertProposals([]);
-    expect((await calls.listOpen(threadId)).map((row) => row.id)).toEqual(['c1', 'c2']);
+    expect((await calls.listOpen(threadId, AT)).map((row) => row.id)).toEqual(['c1', 'c2']);
+    // Proposed before `notBefore`, a change waits no more, though no sweep has marked it expired yet.
+    expect(await calls.listOpen(threadId, LATER)).toEqual([]);
 
     expect(await calls.claimDecision('c1', threadId + 1, true, AT, LATER)).toBe(false);
     expect(await calls.claimDecision('c1', threadId, true, '2026-10-21 00:00:00', LATER)).toBe(false);

server/tests/unit/nest/assistant/assistant-found-places.service.test.ts

@@ -3,7 +3,7 @@
  * call repositories on a migrated test db: the place comes from the search
  * results stored in the thread, the day must be one of the trip's, and the
  * suggestion is held as a change card in one transaction, refused while a turn
- * runs, while another change waits, or past the per-minute limit.
+ * runs, while another change waits within its day, or past the per-minute limit.
  *
  * Replaced: the trip tools (what the trip reads as), the rate limit, the
  * stream registry and the airports.
@@ -11,6 +11,7 @@
 import { AssistantMessages } from '../../../../src/db/entities/AssistantMessages.entity';
 import { AssistantThreads } from '../../../../src/db/entities/AssistantThreads.entity';
 import { AssistantToolCalls } from '../../../../src/db/entities/AssistantToolCalls.entity';
+import { dbNow } from '../../../../src/db/types';
 import { AirportsService } from '../../../../src/nest/airports/airports.service';
 import { AssistantFoundPlacesService } from '../../../../src/nest/assistant/assistant-found-places.service';
 import { AssistantStreamRegistry } from '../../../../src/nest/assistant/assistant-stream.registry';
@@ -19,7 +20,7 @@ import { AssistantCardContext } from '../../../../src/nest/assistant/cards/card-
 import { RateLimitService } from '../../../../src/nest/common/rate-limit.service';
 import { UnitOfWork } from '../../../../src/nest/database/unit-of-work';
 import { createSnapshotTestDb } from '../../../helpers/db-mock';
-import { createRow, findRows } from '../../../helpers/factories/rows';
+import { createRow, findRows, updateRows } from '../../../helpers/factories/rows';
 import { makeTrip } from '../../../helpers/factories/trips';
 import { makeUser } from '../../../helpers/factories/users';
 import { resetTestDb } from '../../../helpers/test-db';
@@ -182,6 +183,19 @@ describe('AssistantFoundPlacesService', () => {
     expect(await calls(c.threadId)).toHaveLength(1);
   });
 
+  it('ASTFND-008: a change left waiting past its day holds nothing back, before the nightly sweep marks it', async () => {
+    const c = await conversation();
+    await add(c, 's1:0');
+    const [stale] = await calls(c.threadId);
+    const dayAndHourAgo = dbNow(new Date(Date.now() - 25 * 60 * 60_000));
+    await updateRows(t.get(MikroORM), AssistantToolCalls, { id: stale?.id ?? '' }, { created_at: dayAndHourAgo });
+
+    await add(c, 's1:1');
+    const held = await calls(c.threadId);
+    expect(held).toHaveLength(2);
+    expect(held.map((call) => call.state)).toEqual(['approval_requested', 'approval_requested']);
+  });
+
   it('ASTFND-007: a ref outside the search results or a day of another trip proposes nothing', async () => {
     const c = await conversation();
     await expect(add(c, 's9:0')).rejects.toMatchObject({ status: 400, code: 'generic' });

server/tests/unit/nest/assistant/assistant-proposals.service.test.ts

@@ -3,7 +3,7 @@
  * and tool call repositories on a migrated test db: the proposal comes from
  * the call and card stored in the thread, never from the request, and the
  * change that creates it is held as a card in one transaction, refused while
- * a turn runs, while another change waits, for a proposal the thread does not
+ * a turn runs, while another change waits within its day, for a proposal the thread does not
  * hold and for one nothing can be created from. A walk is asked again, since
  * the stored answer is the model's shortened copy.
  *
@@ -13,6 +13,7 @@
 import { AssistantMessages } from '../../../../src/db/entities/AssistantMessages.entity';
 import { AssistantThreads } from '../../../../src/db/entities/AssistantThreads.entity';
 import { AssistantToolCalls } from '../../../../src/db/entities/AssistantToolCalls.entity';
+import { dbNow } from '../../../../src/db/types';
 import { AirportsService } from '../../../../src/nest/airports/airports.service';
 import {
   AssistantProposalsService,
@@ -27,7 +28,7 @@ import { RateLimitService } from '../../../../src/nest/common/rate-limit.service
 import { UnitOfWork } from '../../../../src/nest/database/unit-of-work';
 import { tourRouteCard } from '../../../helpers/assistant-tour-cards';
 import { createSnapshotTestDb } from '../../../helpers/db-mock';
-import { createRow, findRows } from '../../../helpers/factories/rows';
+import { createRow, findRows, updateRows } from '../../../helpers/factories/rows';
 import { makeTrip } from '../../../helpers/factories/trips';
 import { makeUser } from '../../../helpers/factories/users';
 import { resetTestDb } from '../../../helpers/test-db';
@@ -226,6 +227,19 @@ describe('AssistantProposalsService', () => {
     expect(await calls(c.threadId)).toHaveLength(1);
   });
 
+  it('ASTPROP-011: a change left waiting past its day holds nothing back, before the nightly sweep marks it', async () => {
+    const c = await conversation();
+    await take(c, 'h1');
+    const [stale] = await calls(c.threadId);
+    const dayAndHourAgo = dbNow(new Date(Date.now() - 25 * 60 * 60_000));
+    await updateRows(t.get(MikroORM), AssistantToolCalls, { id: stale?.id ?? '' }, { created_at: dayAndHourAgo });
+
+    await take(c, 'w1');
+    const held = await calls(c.threadId);
+    expect(held).toHaveLength(2);
+    expect(held.map((call) => call.state)).toEqual(['approval_requested', 'approval_requested']);
+  });
+
   it('ASTPROP-008: a walk stored cut down and masked is created from the tool asked again, named and on no day', async () => {
     const c = await conversation();
     await take(c, 'w1');