ci: re-trigger checks (transient Alpine CDN DNS flake in docker build)

An exact duplicate active waitlist entry (same client/pet/service/
preferred date+time) violates the partial unique index
idx_waitlist_active_unique, which postgres-js surfaces as SQLSTATE
23505. The POST /portal/waitlist handler did not catch it, so the
duplicate returned a generic 500. Catch 23505 specifically and return
409 with a friendly message; unrelated errors still surface as 500 and
the first insert still returns 201.

Adds integration coverage: 201 first insert, 409 duplicate, 500 unrelated.

UAT_PLAYBOOK.md

@@ -165,8 +165,6 @@ Geocoding turns a client's street address into `latitude`/`longitude` + `geocode
 | TC-API-3.19b | Get pet profile summary — customer cross-tenant blocked (GRO-2013) | Sign in as `uat-customer@groombook.dev`; reuse the customer's sessionId from TC-API-3.19a; `GET /api/pets/{otherClientPetId}/profile-summary` for a pet owned by a different client (`c0000002-...` or any non-customer pet) | 403 Forbidden (owner-bypass requires session.clientId === pet.clientId) |
 | TC-API-3.19c | Get pet profile summary — customer without portal session header | Same as TC-API-3.19a but omit the `X-Impersonation-Session-Id` header | 403 Forbidden (no owner-bypass without valid portal session) |
 | TC-API-3.19d | Get pet profile summary — owner-bypass writes audit row (GRO-2063) | Same setup as TC-API-3.19a (sign in as `uat-customer@groombook.dev`, establish a portal session for the customer's own clientId, call `GET /api/pets/{ownPetId}/profile-summary` with `X-Impersonation-Session-Id: {sessionId}` and a 200 OK response). Then call `GET /api/impersonation/sessions/{sessionId}/audit-log` and confirm there is exactly one entry with `action === "read_profile_summary"`, `pageVisited` matching the profile-summary path, and `metadata` containing `petId` and `actorStaffId` for the customer. Repeat TC-API-3.19b (cross-tenant attempt) and confirm NO new `read_profile_summary` row was written for the cross-tenant attempt. | 200 OK on the profile-summary call AND an audit log entry is present with the correct shape (defense-in-depth audit row; bypass attempts against other clients must NOT log) |
-| TC-UAT-2 | Groomer accesses linked pet profile summary (GRO-2100) | Sign in as `uat-groomer@groombook.dev`; `GET /api/pets/c0000001-0000-0000-0000-000000000002/profile-summary` (UAT Pup Alpha — linked via deterministic completed appointment `a0000001-0000-0000-0000-000000000001`, service `b0000001-…-0001` "Bath & Brush", `startTime` ~7 days ago) | 200 OK, `recentGroomingHistory[]` non-empty (>=1 entry), `visitCount >= 1`, `upcomingAppointment` null (the seeded appointment is in the past) |
-| TC-UAT-3 | Groomer blocked from unlinked pet profile summary (GRO-2100) | Sign in as `uat-groomer@groombook.dev`; `GET /api/pets/c0000001-0000-0000-0000-000000000003/profile-summary` (UAT Pup Beta — intentionally UNLINKED; no appointment row references this pet's clientId+groomerId combo) | 403 Forbidden (RBAC `groomer` role lacks the appointment-linkage grant for this pet). NOTE: if 404 is returned instead of 403, file a separate RBAC defect (not against the seed) — see GRO-2100 verification note |
 | TC-API-3.29 | Get pet profile summary — unknown UUID returns 404 (GRO-2014) | GET /api/pets/00000000-0000-0000-0000-000000000001/profile-summary while authenticated (any role) | 404 Not Found with body `{"error":"Not found"}` (was empty-body 500 in GRO-2014) |
 | TC-API-3.30 | Get pet profile summary — malformed UUID returns 404 (GRO-2014) | GET /api/pets/not-a-uuid/profile-summary while authenticated | 404 Not Found with body `{"error":"Not found"}` (was empty-body 500 in GRO-2014 — Postgres uuid cast failure) |
 | TC-API-3.31 | Get pet profile summary — never empty-body 500 (GRO-2014) | GET /api/pets/{anyId}/profile-summary across the test sweep | No response has status 500 with an empty body. Any 500 must include a JSON body `{"error":"Internal Server Error"}` |
@@ -284,6 +282,8 @@ This means:
 | TC-API-8.14 | Portal pet update — non-owner blocked (GRO-2187) | `PATCH /api/portal/pets/{petId}` for a pet owned by a different client, using another client's portal session | 403 Forbidden (or 404 if pet id is unknown); no mutation persisted |
 | TC-API-8.15 | Portal pet update — invalid enum rejected (GRO-2187) | `PATCH /api/portal/pets/{petId}` with `coatType: "fluffy"` or `petSizeCategory: "gigantic"` | 422 Unprocessable Entity; pet unchanged |
 | TC-API-8.16 | Portal pet update — malformed (non-UUID) petId returns 404 (GRO-2203) | With a valid portal session, `PATCH /api/portal/pets/not-a-uuid` with header `X-Impersonation-Session-Id` and body `{"coatType":"short"}` | 404 Not Found with body `{"error":"Not found"}` (was an unhandled 500 from the Postgres uuid cast in GRO-2203; mirrors the GRO-2014 guard). No mutation persisted |
+| TC-API-8.17 | SSO portal session slides on activity (GRO-2234) | Establish a portal session (TC-API-8.8). Note the returned `sessionId`. Make any authenticated portal call (e.g. `GET /api/portal/me`) several times spaced over ≥1 minute, each with `X-Impersonation-Session-Id: {sessionId}`. | Every call returns 200; the session's `expiresAt` is extended (slid forward to ~30 min from each request) so the session stays valid during continuous use — it does NOT lapse mid-session. SSO-bridge sessions mint with a 30-min idle TTL bounded by an 8h absolute cap from `startedAt`. |
+| TC-API-8.18 | Slow-wizard Book New submit succeeds (GRO-2234) | Establish a portal session (TC-API-8.8). Wait >2 minutes while making at least one intervening authenticated portal call (mimicking the multi-step Book New wizard: pet/service/groomer/date GETs). Then `POST /api/portal/waitlist` with a valid pet+service payload and the same `X-Impersonation-Session-Id`. | 201 Created — the deliberately-paced wizard no longer 401s on submit because activity slid the session forward. (Regression guard for the GRO-2234 "session TTL too short → 401" defect.) |
 
 ### 4.9 Waitlist
 
@@ -363,7 +363,12 @@ This means:
 
 ### 4.16 Route Optimization — Route CRUD + Optimize (GRO-2155, Phase 2.1)
 
-A groomer's daily route is one row per `(staffId, routeDate)` in `groomer_routes`, with ordered `route_stops`. `POST /api/routes/optimize` pulls the day's non-cancelled appointments whose client is geocoded (GRO-2154), orders them (Google Directions `optimizeWaypoints` when a key is configured in `businessSettings.googleMapsApiKey`, else an offline nearest-neighbor heuristic), and persists `stopOrder`, `travelMinsFromPrev`, `travelDistanceKmFromPrev` plus route `totalTravelMins`/`totalDistanceKm`/`optimizedAt`. **Auth: manager (any groomer's route) or groomer (own route only); receptionists have no access.** Pre-condition: at least one geocoded client with appointments on the target date for the staff member (use §4.2 geocoding + a seed groomer).
+A groomer's daily route is one row per `(staffId, routeDate)` in `groomer_routes`, with ordered `route_stops`. `POST /api/routes/optimize` pulls the day's non-cancelled appointments whose client is geocoded (GRO-2154), orders them (Google Directions `optimizeWaypoints` when a key is configured in `businessSettings.googleMapsApiKey`, else an offline nearest-neighbor heuristic), and persists `stopOrder`, `travelMinsFromPrev`, `travelDistanceKmFromPrev` plus route `totalTravelMins`/`totalDistanceKm`/`optimizedAt`. **Auth: manager (any groomer's route) or groomer (own route only); receptionists have no access.**
+
+**Pre-condition (GRO-2225 — zero-touch; no manual PATCH/geocoding needed).** A fresh UAT reset+seed now provisions a deterministic route cohort, so §4.16 runs directly against seed data:
+- **Groomer:** `uat-groomer@groombook.dev` (staffId `00000000-0000-0000-0000-000000000004`). Resolve its id via `GET /api/staff` or sign in as the groomer and omit `staffId`.
+- **Date:** `2026-09-15` (fixed). On this date the groomer has **12** confirmed appointments: **10 pre-geocoded** clients clustered in the Seattle metro (multi-stop route) + **2 intentionally un-geocoded** clients (exercise the skip-and-surface path, TC-API-16.4). Cohort clients are named `Route Demo — …` (emails `route-client-NN@uat.groombook.dev`).
+- **Receptionist (TC-API-16.9 403):** sign in as `uat-receptionist@groombook.dev` (password from the `seed-uat-passwords` secret, key `SEED_UAT_RECEPTIONIST_PASSWORD`) — a standing receptionist login; no hand-built session required.
 
 | # | Scenario | Steps | Expected |
 |---|----------|-------|----------|

packages/db/src/seed.ts

@@ -456,6 +456,36 @@ async function seedUatStaffAccounts(
     }
   }
 
+  // ── Staff: UAT Receptionist (GRO-2225) ──────────────────────────────────────
+  // Standing receptionist staff record so the route-optimization 403 path
+  // (TC-API-16.9: receptionist GET/POST /api/routes → 403) is reproducible
+  // without a hand-built session. The matching Better-Auth credential is
+  // provisioned below from SEED_UAT_RECEPTIONIST_PASSWORD. Created here (gated
+  // on the password env) so the credential loop's staff-link step finds it.
+  if (process.env.SEED_UAT_RECEPTIONIST_PASSWORD) {
+    const UAT_RECEPTIONIST_STAFF_ID = "00000000-0000-0000-0000-000000000099";
+    const [existingReceptionist] = await db
+      .select()
+      .from(schema.staff)
+      .where(eq(schema.staff.email, "uat-receptionist@groombook.dev"))
+      .limit(1);
+
+    if (existingReceptionist) {
+      console.log(`✓ Staff 'UAT Receptionist' already exists — skipping`);
+    } else {
+      await db.insert(schema.staff).values({
+        id: UAT_RECEPTIONIST_STAFF_ID,
+        name: "UAT Receptionist",
+        email: "uat-receptionist@groombook.dev",
+        oidcSub: "uat-receptionist@groombook.dev",
+        role: "receptionist",
+        isSuperUser: false,
+        active: true,
+      });
+      console.log(`✓ Created staff 'UAT Receptionist' (uat-receptionist@groombook.dev)`);
+    }
+  }
+
   // ── Staff: UAT Groomer Personas (SEED_UAT_GROOMER_EMAILS + SEED_UAT_GROOMER_NAMES) ──
   const groomerEmails = process.env.SEED_UAT_GROOMER_EMAILS?.split(",").map((e) => e.trim()).filter(Boolean) ?? [];
   const groomerNames = process.env.SEED_UAT_GROOMER_NAMES?.split(",").map((n) => n.trim()).filter(Boolean) ?? [];
@@ -495,6 +525,8 @@ async function seedUatStaffAccounts(
     { email: "uat-groomer@groombook.dev", name: "UAT Staff Groomer", passwordEnv: "SEED_UAT_GROOMER_PASSWORD", staffEmail: "uat-groomer@groombook.dev" },
     { email: "uat-customer@groombook.dev", name: "UAT Customer", passwordEnv: "SEED_UAT_CUSTOMER_PASSWORD", staffEmail: null },
     { email: "uat-tester@groombook.dev", name: "UAT Tester", passwordEnv: "SEED_UAT_TESTER_PASSWORD", staffEmail: "uat-tester@groombook.dev" },
+    // GRO-2225: standing receptionist login for the route-optimization 403 path (TC-API-16.9).
+    { email: "uat-receptionist@groombook.dev", name: "UAT Receptionist", passwordEnv: "SEED_UAT_RECEPTIONIST_PASSWORD", staffEmail: "uat-receptionist@groombook.dev" },
   ];
 
   for (const acct of uatPasswordAccounts) {
@@ -798,6 +830,179 @@ async function seedUatGroomerLinkage(
   );
 }
 
+// ── GRO-2225: deterministic route-optimization cohort ────────────────────────
+
+/**
+ * GRO-2225: seed a deterministic, pre-geocoded client cohort + a fixed-date set
+ * of appointments for the UAT groomer so the route-optimization endpoints
+ * (`GET /api/routes/daily`, `POST /api/routes/optimize`, UAT §4.16
+ * TC-API-16.1…16.11) are exercisable with ZERO manual PATCHing.
+ *
+ * Design (no live geocoder — UAT has no Google Maps key, provider is
+ * nearest_neighbor; coordinates are hand-picked fixtures clustered in the
+ * Seattle metro):
+ *   - All appointments are on a FIXED calendar date (ROUTE_DATE) and assigned to
+ *     the UAT groomer (`uat-groomer@groombook.dev`). The optimize endpoint pulls
+ *     non-cancelled appointments in [date 00:00Z, +24h) joined to client coords.
+ *   - 10 clients carry deterministic lat/lng → a multi-stop optimized route.
+ *   - 2 clients are intentionally left UN-geocoded so the "skipped + surfaced"
+ *     path (TC-API-16.5) stays reproducible.
+ *
+ * Idempotent: clients/pets are upserted by fixed UUID (they are NOT truncated on
+ * reset); appointments are upserted by fixed UUID too (they ARE truncated on
+ * reset, but the upsert keeps re-runs safe in non-truncating dev/test paths).
+ * Skips cleanly when the UAT groomer staff record is absent (e.g. prod/demo or a
+ * dev seed without the UAT personas).
+ */
+async function seedUatRouteCohort(db: ReturnType<typeof drizzle>): Promise<void> {
+  // Fixed calendar date the UAT playbook hardcodes for §4.16. Times are UTC so
+  // they fall inside the optimize endpoint's [date 00:00Z, +24h) day window.
+  const ROUTE_DATE = "2026-09-15";
+
+  const [uatGroomer] = await db
+    .select({ id: schema.staff.id })
+    .from(schema.staff)
+    .where(eq(schema.staff.email, "uat-groomer@groombook.dev"))
+    .limit(1);
+  if (!uatGroomer) {
+    console.log("✓ GRO-2225: uat-groomer not present — skipping route cohort");
+    return;
+  }
+
+  // Resolve a service for the appointments: prefer Bath & Brush, else any active.
+  const BATH_AND_BRUSH_ID = "b0000001-0000-0000-0000-000000000001";
+  const [bathService] = await db
+    .select({ id: schema.services.id })
+    .from(schema.services)
+    .where(eq(schema.services.id, BATH_AND_BRUSH_ID))
+    .limit(1);
+  let serviceId: string;
+  if (bathService) {
+    serviceId = bathService.id;
+  } else {
+    const [fallback] = await db
+      .select({ id: schema.services.id })
+      .from(schema.services)
+      .where(eq(schema.services.active, true))
+      .limit(1);
+    if (!fallback) {
+      console.warn("⚠ GRO-2225: no active services found — skipping route cohort");
+      return;
+    }
+    serviceId = fallback.id;
+  }
+
+  // Hand-picked fixture coordinates clustered in the Seattle metro. `coords:null`
+  // marks an intentionally un-geocoded client (skip-and-surface path TC-16.5).
+  const cohort: Array<{
+    n: number;
+    name: string;
+    coords: { lat: number; lng: number } | null;
+  }> = [
+    { n: 1, name: "Route Demo — Ada Lovelace", coords: { lat: 47.6097, lng: -122.3331 } },
+    { n: 2, name: "Route Demo — Grace Hopper", coords: { lat: 47.6205, lng: -122.3493 } },
+    { n: 3, name: "Route Demo — Alan Turing", coords: { lat: 47.5990, lng: -122.3300 } },
+    { n: 4, name: "Route Demo — Katherine Johnson", coords: { lat: 47.6150, lng: -122.3200 } },
+    { n: 5, name: "Route Demo — Edsger Dijkstra", coords: { lat: 47.6280, lng: -122.3550 } },
+    { n: 6, name: "Route Demo — Barbara Liskov", coords: { lat: 47.5920, lng: -122.3150 } },
+    { n: 7, name: "Route Demo — Donald Knuth", coords: { lat: 47.6350, lng: -122.3400 } },
+    { n: 8, name: "Route Demo — Margaret Hamilton", coords: { lat: 47.6050, lng: -122.3600 } },
+    { n: 9, name: "Route Demo — Ken Thompson", coords: { lat: 47.6420, lng: -122.3250 } },
+    { n: 10, name: "Route Demo — Radia Perlman", coords: { lat: 47.5880, lng: -122.3450 } },
+    // Intentionally un-geocoded — exercises the skip-and-surface path.
+    { n: 11, name: "Route Demo — Ungeocoded One", coords: null },
+    { n: 12, name: "Route Demo — Ungeocoded Two", coords: null },
+  ];
+
+  // Stagger appointments 45 min apart starting 15:00Z on ROUTE_DATE.
+  const dayStartMs = new Date(`${ROUTE_DATE}T15:00:00.000Z`).getTime();
+  const SLOT_MS = 45 * 60 * 1000;
+
+  let geocodedCount = 0;
+  let ungeocodedCount = 0;
+  for (const c of cohort) {
+    const pad = String(c.n).padStart(2, "0");
+    const clientId = `d0000000-0000-0000-0000-0000000000${pad}`;
+    const petId = `d0000000-0000-0000-0000-0000000001${pad}`;
+    const apptId = `d0000000-0000-0000-0000-0000000002${pad}`;
+    const geocodedAt = c.coords ? new Date(`${ROUTE_DATE}T00:00:00.000Z`) : null;
+
+    await db.insert(schema.clients)
+      .values({
+        id: clientId,
+        name: c.name,
+        email: `route-client-${pad}@uat.groombook.dev`,
+        phone: `(206) 555-01${pad}`,
+        address: `${100 + c.n} Pike Street, Seattle, WA 98101`,
+        status: "active",
+        latitude: c.coords?.lat ?? null,
+        longitude: c.coords?.lng ?? null,
+        geocodedAt,
+      })
+      .onConflictDoUpdate({
+        target: schema.clients.id,
+        set: {
+          name: c.name,
+          address: `${100 + c.n} Pike Street, Seattle, WA 98101`,
+          latitude: c.coords?.lat ?? null,
+          longitude: c.coords?.lng ?? null,
+          geocodedAt,
+        },
+      });
+
+    await db.insert(schema.pets)
+      .values({
+        id: petId,
+        clientId,
+        name: `Route Pup ${c.n}`,
+        species: "Dog",
+        breed: "Mixed",
+        weightKg: "18.00",
+      })
+      .onConflictDoUpdate({
+        target: schema.pets.id,
+        set: { clientId, name: `Route Pup ${c.n}`, species: "Dog" },
+      });
+
+    const startTime = new Date(dayStartMs + (c.n - 1) * SLOT_MS);
+    const endTime = new Date(startTime.getTime() + SLOT_MS);
+    await db.insert(schema.appointments)
+      .values({
+        id: apptId,
+        clientId,
+        petId,
+        serviceId,
+        staffId: uatGroomer.id,
+        batherStaffId: null,
+        status: "confirmed",
+        startTime,
+        endTime,
+        notes: "GRO-2225: deterministic route-optimization cohort appointment.",
+        priceCents: null,
+        confirmationStatus: "confirmed",
+      })
+      .onConflictDoUpdate({
+        target: schema.appointments.id,
+        set: {
+          clientId,
+          petId,
+          serviceId,
+          staffId: uatGroomer.id,
+          status: "confirmed",
+          startTime,
+          endTime,
+        },
+      });
+
+    if (c.coords) geocodedCount++;
+    else ungeocodedCount++;
+  }
+
+  console.log(
+    `✓ GRO-2225: seeded route cohort for ${ROUTE_DATE} — ${geocodedCount} geocoded + ${ungeocodedCount} un-geocoded appointment(s) for uat-groomer (${uatGroomer.id})`,
+  );
+}
+
 // ── Known-users-only seed (prod/demo) ───────────────────────────────────────
 
 /**
@@ -1169,6 +1374,11 @@ async function runSeedBody(
   // the time seedUatStaffAccounts() returns).
   await seedUatGroomerLinkage(db, uatCustomerClientId);
 
+  // GRO-2225: deterministic pre-geocoded route cohort + fixed-date appointments
+  // for the UAT groomer. Must run AFTER services are seeded (it looks up a
+  // service id for the appointments). Skips cleanly if uat-groomer is absent.
+  await seedUatRouteCohort(db);
+
   // ── Clients & Pets ──
   const now = new Date();
   const appointmentsBackDate = new Date(now);

src/__tests__/portalSessionSliding.test.ts

@@ -0,0 +1,188 @@
+import { describe, it, expect, beforeEach, vi } from "vitest";
+import { Hono } from "hono";
+import {
+  validatePortalSession,
+  PORTAL_SESSION_IDLE_TTL_MS,
+  PORTAL_SESSION_MAX_LIFETIME_MS,
+  type PortalEnv,
+} from "../middleware/portalSession.js";
+
+const SESSION_ID = "770e8400-e29b-41d4-a716-446655440003";
+const CLIENT_ID = "550e8400-e29b-41d4-a716-446655440001";
+
+// Mutable test state driven per-case.
+let selectSessionRow: Record<string, unknown> | null = null;
+let sessionUpdates: Record<string, unknown>[] = [];
+
+function resetMock() {
+  selectSessionRow = null;
+  sessionUpdates = [];
+}
+
+vi.mock("@groombook/db", () => {
+  function makeChainable(data: unknown[]): unknown {
+    const arr = [...data];
+    const chain = new Proxy(arr, {
+      get(target, prop) {
+        if (prop === "where" || prop === "orderBy" || prop === "limit") {
+          return () => chain;
+        }
+        // @ts-expect-error proxy index
+        return target[prop];
+      },
+    });
+    return chain;
+  }
+
+  const impersonationSessions = new Proxy(
+    { _name: "impersonationSessions" },
+    { get: (t, p) => (p === "_name" ? "impersonationSessions" : { table: "impersonationSessions", column: p }) }
+  );
+
+  return {
+    getDb: () => ({
+      select: () => ({
+        from: (table: { _name: string }) => {
+          if (table._name === "impersonationSessions") {
+            return makeChainable(selectSessionRow ? [selectSessionRow] : []);
+          }
+          return makeChainable([]);
+        },
+      }),
+      update: () => ({
+        set: (vals: Record<string, unknown>) => {
+          sessionUpdates.push(vals);
+          return { where: () => Promise.resolve(undefined) };
+        },
+      }),
+    }),
+    impersonationSessions,
+    eq: vi.fn(),
+    and: vi.fn(),
+  };
+});
+
+const app = new Hono<PortalEnv>();
+app.use("/portal/*", validatePortalSession);
+app.get("/portal/ping", (c) => c.json({ ok: true, clientId: c.get("portalClientId") }));
+
+function ping(headers?: Record<string, string>) {
+  return app.request("/portal/ping", { method: "GET", headers });
+}
+
+beforeEach(() => resetMock());
+
+describe("validatePortalSession — sliding expiration (GRO-2234)", () => {
+  it("extends an sso-bridge session's expiresAt on each authenticated request", async () => {
+    const now = Date.now();
+    // Session minted ~28 min ago, originally a 30-min idle window: it is still
+    // valid (2 min left) but a slow wizard would otherwise let it lapse.
+    selectSessionRow = {
+      id: SESSION_ID,
+      clientId: CLIENT_ID,
+      status: "active",
+      reason: "sso-bridge",
+      startedAt: new Date(now - 28 * 60 * 1000),
+      expiresAt: new Date(now + 2 * 60 * 1000),
+    };
+
+    const res = await ping({ "X-Impersonation-Session-Id": SESSION_ID });
+    expect(res.status).toBe(200);
+
+    expect(sessionUpdates).toHaveLength(1);
+    const newExpiry = sessionUpdates[0]!.expiresAt as Date;
+    // Slid forward to ~now + 30 min (well past the original 2-min-left window).
+    expect(newExpiry.getTime()).toBeGreaterThan(now + PORTAL_SESSION_IDLE_TTL_MS - 5_000);
+    expect(newExpiry.getTime()).toBeLessThanOrEqual(now + PORTAL_SESSION_IDLE_TTL_MS + 5_000);
+  });
+
+  it("keeps a slow-wizard customer authorized past the original mint TTL", async () => {
+    const now = Date.now();
+    // Original mint window has fully elapsed in wall-clock terms, but the session
+    // was slid forward on the previous request, so it is still valid now.
+    selectSessionRow = {
+      id: SESSION_ID,
+      clientId: CLIENT_ID,
+      status: "active",
+      reason: "sso-bridge",
+      startedAt: new Date(now - 35 * 60 * 1000),
+      expiresAt: new Date(now + 10 * 60 * 1000), // previously slid
+    };
+
+    const res = await ping({ "X-Impersonation-Session-Id": SESSION_ID });
+    expect(res.status).toBe(200);
+    const body = await res.json();
+    expect(body.clientId).toBe(CLIENT_ID);
+  });
+
+  it("never extends beyond startedAt + MAX_LIFETIME (bounded)", async () => {
+    const now = Date.now();
+    // Session started right at the absolute cap boundary minus a hair.
+    const startedAt = now - (PORTAL_SESSION_MAX_LIFETIME_MS - 5 * 60 * 1000);
+    selectSessionRow = {
+      id: SESSION_ID,
+      clientId: CLIENT_ID,
+      status: "active",
+      reason: "sso-bridge",
+      startedAt: new Date(startedAt),
+      expiresAt: new Date(now + 60 * 1000),
+    };
+
+    const res = await ping({ "X-Impersonation-Session-Id": SESSION_ID });
+    expect(res.status).toBe(200);
+    expect(sessionUpdates).toHaveLength(1);
+    const newExpiry = (sessionUpdates[0]!.expiresAt as Date).getTime();
+    // Capped at startedAt + MAX_LIFETIME, NOT now + IDLE_TTL.
+    expect(newExpiry).toBeLessThanOrEqual(startedAt + PORTAL_SESSION_MAX_LIFETIME_MS + 1_000);
+    expect(newExpiry).toBeGreaterThan(now); // still extends at least a little
+  });
+
+  it("does NOT slide a staff-initiated impersonation session (no regression)", async () => {
+    const now = Date.now();
+    selectSessionRow = {
+      id: SESSION_ID,
+      clientId: CLIENT_ID,
+      status: "active",
+      reason: "manager reviewing booking", // staff-console reason, free text
+      startedAt: new Date(now - 5 * 60 * 1000),
+      expiresAt: new Date(now + 20 * 60 * 1000),
+    };
+
+    const res = await ping({ "X-Impersonation-Session-Id": SESSION_ID });
+    expect(res.status).toBe(200);
+    expect(sessionUpdates).toHaveLength(0);
+  });
+
+  it("still rejects an already-expired session (no resurrection)", async () => {
+    const now = Date.now();
+    selectSessionRow = {
+      id: SESSION_ID,
+      clientId: CLIENT_ID,
+      status: "active",
+      reason: "sso-bridge",
+      startedAt: new Date(now - 40 * 60 * 1000),
+      expiresAt: new Date(now - 60 * 1000), // already lapsed
+    };
+
+    const res = await ping({ "X-Impersonation-Session-Id": SESSION_ID });
+    expect(res.status).toBe(401);
+    expect(sessionUpdates).toHaveLength(0);
+  });
+
+  it("skips the write when the extension is below the slide threshold", async () => {
+    const now = Date.now();
+    // Already slid this minute: expiresAt is essentially now + IDLE_TTL already.
+    selectSessionRow = {
+      id: SESSION_ID,
+      clientId: CLIENT_ID,
+      status: "active",
+      reason: "sso-bridge",
+      startedAt: new Date(now - 2 * 60 * 1000),
+      expiresAt: new Date(now + PORTAL_SESSION_IDLE_TTL_MS - 2_000),
+    };
+
+    const res = await ping({ "X-Impersonation-Session-Id": SESSION_ID });
+    expect(res.status).toBe(200);
+    expect(sessionUpdates).toHaveLength(0);
+  });
+});

src/__tests__/portalWaitlistDuplicate.test.ts

@@ -0,0 +1,154 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { Hono } from "hono";
+
+// GRO-2235: a duplicate active waitlist entry violates the partial unique index
+// idx_waitlist_active_unique. postgres-js surfaces it as SQLSTATE 23505 — the
+// handler must return a friendly 409, not a generic 500. The first insert still
+// returns 201, and unrelated errors still surface as 500.
+
+const CLIENT_ID = "550e8400-e29b-41d4-a716-446655440001";
+const SESSION_ID = "770e8400-e29b-41d4-a716-446655440003";
+const PET_ID = "880e8400-e29b-41d4-a716-446655440004";
+const SERVICE_ID = "990e8400-e29b-41d4-a716-446655440005";
+
+const futureDate = () => new Date(Date.now() + 30 * 60 * 1000);
+
+const ACTIVE_SESSION = {
+  id: SESSION_ID,
+  clientId: CLIENT_ID,
+  status: "active" as const,
+  reason: "manual",
+  startedAt: new Date(),
+  expiresAt: futureDate(),
+  createdAt: new Date(),
+};
+
+// Behaviour knob for the waitlist insert: "ok" returns a row, "duplicate" throws
+// a postgres-js-shaped unique-violation, "other" throws an unrelated error.
+let waitlistInsertMode: "ok" | "duplicate" | "other" = "ok";
+
+function resetMock() {
+  waitlistInsertMode = "ok";
+}
+
+function tableProxy(name: string) {
+  return new Proxy(
+    { _name: name },
+    { get: (t, p) => (p === "_name" ? name : { table: name, column: p }) }
+  );
+}
+
+vi.mock("@groombook/db", () => {
+  function makeChainable(data: unknown[]): unknown {
+    const arr = [...data];
+    const chain = new Proxy(arr, {
+      get(target, prop) {
+        if (prop === "where" || prop === "orderBy" || prop === "limit") {
+          return () => chain;
+        }
+        // @ts-expect-error proxy
+        return target[prop];
+      },
+    });
+    return chain;
+  }
+
+  const impersonationSessions = tableProxy("impersonationSessions");
+  const waitlistEntries = tableProxy("waitlistEntries");
+  const impersonationAuditLogs = tableProxy("impersonationAuditLogs");
+
+  return {
+    getDb: () => ({
+      select: () => ({
+        from: (table: { _name: string }) => {
+          if (table._name === "impersonationSessions") {
+            return makeChainable([ACTIVE_SESSION]);
+          }
+          return makeChainable([]);
+        },
+      }),
+      insert: (table: { _name: string }) => ({
+        values: (vals: Record<string, unknown>) => ({
+          returning: () => {
+            if (table._name === "waitlistEntries") {
+              if (waitlistInsertMode === "duplicate") {
+                throw Object.assign(new Error("duplicate key value"), { code: "23505" });
+              }
+              if (waitlistInsertMode === "other") {
+                throw Object.assign(new Error("not null violation"), { code: "23502" });
+              }
+              return [{ id: "entry-1", ...vals }];
+            }
+            // impersonationAuditLogs and anything else: succeed silently.
+            return [{ id: "audit-1", ...vals }];
+          },
+        }),
+      }),
+      update: () => ({
+        set: () => ({ where: () => Promise.resolve() }),
+      }),
+    }),
+    impersonationSessions,
+    waitlistEntries,
+    impersonationAuditLogs,
+    appointments: tableProxy("appointments"),
+    clients: tableProxy("clients"),
+    pets: tableProxy("pets"),
+    services: tableProxy("services"),
+    staff: tableProxy("staff"),
+    invoices: tableProxy("invoices"),
+    invoiceLineItems: tableProxy("invoiceLineItems"),
+    eq: vi.fn(),
+    and: vi.fn(),
+    inArray: vi.fn(),
+  };
+});
+
+const { portalRouter } = await import("../routes/portal.js");
+
+const app = new Hono();
+app.route("/portal", portalRouter);
+
+function postWaitlist(body: unknown) {
+  return app.request("/portal/waitlist", {
+    method: "POST",
+    headers: {
+      "Content-Type": "application/json",
+      "X-Impersonation-Session-Id": SESSION_ID,
+    },
+    body: JSON.stringify(body),
+  });
+}
+
+const VALID_BODY = {
+  petId: PET_ID,
+  serviceId: SERVICE_ID,
+  preferredDate: "2026-07-01",
+  preferredTime: "09:00",
+};
+
+beforeEach(() => resetMock());
+
+describe("POST /portal/waitlist duplicate handling (GRO-2235)", () => {
+  it("returns 201 for the first insert", async () => {
+    waitlistInsertMode = "ok";
+    const res = await postWaitlist(VALID_BODY);
+    expect(res.status).toBe(201);
+  });
+
+  it("returns 409 with a friendly message for a duplicate (23505)", async () => {
+    waitlistInsertMode = "duplicate";
+    const res = await postWaitlist(VALID_BODY);
+    expect(res.status).toBe(409);
+    const json = (await res.json()) as { error: string };
+    expect(json.error).toBe(
+      "You already have a booking for this pet at that date and time."
+    );
+  });
+
+  it("still surfaces unrelated DB errors as 500", async () => {
+    waitlistInsertMode = "other";
+    const res = await postWaitlist(VALID_BODY);
+    expect(res.status).toBe(500);
+  });
+});

src/middleware/portalSession.ts

@@ -8,6 +8,32 @@ export interface PortalEnv {
   };
 }
 
+/**
+ * Idle lifetime of an SSO-bridge portal impersonation session. Each authenticated
+ * portal request slides `expiresAt` forward to `now + IDLE_TTL`, so an actively-used
+ * session (e.g. a customer working through the multi-step Book New wizard) never
+ * lapses mid-flow. Matches the staff-console impersonation idle window
+ * (SESSION_TIMEOUT_MINUTES in routes/impersonation.ts). (GRO-2234)
+ */
+export const PORTAL_SESSION_IDLE_TTL_MS = 30 * 60 * 1000;
+
+/**
+ * Absolute cap on a single SSO-bridge portal session's lifetime, measured from
+ * `startedAt`. Sliding can never extend a session beyond this bound, keeping the
+ * impersonation model bounded regardless of how long a customer keeps the tab
+ * active. Deliberately tighter than the previous static 24h mint. (GRO-2234)
+ */
+export const PORTAL_SESSION_MAX_LIFETIME_MS = 8 * 60 * 60 * 1000;
+
+/**
+ * Minimum extension before we issue a sliding-expiration write. Avoids a DB write
+ * on every rapid successive request — at most one slide per minute per session.
+ */
+const PORTAL_SESSION_SLIDE_THRESHOLD_MS = 60 * 1000;
+
+/** Reason marker for sessions minted by the Better Auth -> portal bridge. */
+const SSO_BRIDGE_REASON = "sso-bridge";
+
 /**
  * Validates the X-Impersonation-Session-Id header against the impersonationSessions table.
  * Must be applied to all portal routes.
@@ -16,6 +42,12 @@ export interface PortalEnv {
  * id = sessionId AND status = 'active', and checks session.expiresAt > new Date().
  * Returns 401 if session is invalid/missing/expired.
  * On success, sets c.set("portalClientId", session.clientId) and c.set("portalSessionId", session.id).
+ *
+ * Sliding expiration (GRO-2234): for SSO-bridge sessions, each successful request
+ * extends `expiresAt` to `now + PORTAL_SESSION_IDLE_TTL_MS`, bounded by
+ * `startedAt + PORTAL_SESSION_MAX_LIFETIME_MS`. Staff-initiated impersonation
+ * sessions (any other `reason`) are left untouched, preserving their existing
+ * console-enforced timeout behavior.
  */
 export const validatePortalSession: MiddlewareHandler<PortalEnv> = async (c, next) => {
   const sessionId = c.req.header("X-Impersonation-Session-Id");
@@ -24,16 +56,29 @@ export const validatePortalSession: MiddlewareHandler<PortalEnv> = async (c, nex
   }
 
   const db = getDb();
+  const now = new Date();
   const [session] = await db
     .select()
     .from(impersonationSessions)
     .where(and(eq(impersonationSessions.id, sessionId), eq(impersonationSessions.status, "active")))
     .limit(1);
 
-  if (!session || session.expiresAt <= new Date()) {
+  if (!session || session.expiresAt <= now) {
     return c.json({ error: "Unauthorized" }, 401);
   }
 
+  // Sliding expiration for SSO-bridge portal sessions only (GRO-2234).
+  if (session.reason === SSO_BRIDGE_REASON) {
+    const maxExpiry = session.startedAt.getTime() + PORTAL_SESSION_MAX_LIFETIME_MS;
+    const slidExpiry = Math.min(now.getTime() + PORTAL_SESSION_IDLE_TTL_MS, maxExpiry);
+    if (slidExpiry - session.expiresAt.getTime() >= PORTAL_SESSION_SLIDE_THRESHOLD_MS) {
+      await db
+        .update(impersonationSessions)
+        .set({ expiresAt: new Date(slidExpiry) })
+        .where(eq(impersonationSessions.id, session.id));
+    }
+  }
+
   c.set("portalClientId", session.clientId);
   c.set("portalSessionId", session.id);
   await next();

src/routes/portal.ts

@@ -3,7 +3,7 @@ import { zValidator } from "@hono/zod-validator";
 import { z } from "zod/v3";
 import { eq, inArray } from "@groombook/db";
 import { getDb, appointments, impersonationSessions, waitlistEntries, clients, pets, services, staff, invoices, invoiceLineItems } from "@groombook/db";
-import { validatePortalSession } from "../middleware/portalSession.js";
+import { validatePortalSession, PORTAL_SESSION_IDLE_TTL_MS } from "../middleware/portalSession.js";
 import { portalAudit } from "../middleware/portalAudit.js";
 import type { PortalEnv } from "../middleware/portalSession.js";
 
@@ -129,7 +129,7 @@ portalRouter.post("/session-from-auth", async (c) => {
       staffId,
       clientId: client.id,
       reason: "sso-bridge",
-      expiresAt: new Date(Date.now() + 24 * 60 * 60 * 1000),
+      expiresAt: new Date(Date.now() + PORTAL_SESSION_IDLE_TTL_MS),
     })
     .returning();
 
@@ -596,16 +596,32 @@ portalRouter.post(
     const body = c.req.valid("json");
     const clientId = c.get("portalClientId");
 
-    const [entry] = await db
-      .insert(waitlistEntries)
-      .values({
-        clientId,
-        petId: body.petId,
-        serviceId: body.serviceId,
-        preferredDate: body.preferredDate,
-        preferredTime: normalizeTime(body.preferredTime),
-      })
-      .returning();
+    let entry;
+    try {
+      [entry] = await db
+        .insert(waitlistEntries)
+        .values({
+          clientId,
+          petId: body.petId,
+          serviceId: body.serviceId,
+          preferredDate: body.preferredDate,
+          preferredTime: normalizeTime(body.preferredTime),
+        })
+        .returning();
+    } catch (err) {
+      // An exact duplicate active waitlist entry violates the partial unique
+      // index idx_waitlist_active_unique (client_id, pet_id, service_id,
+      // preferred_date, preferred_time WHERE status='active'). postgres-js
+      // surfaces this as SQLSTATE 23505 — return a friendly 409 rather than a
+      // generic 500 (GRO-2235). Unrelated errors still surface as 500.
+      if ((err as { code?: string })?.code === "23505") {
+        return c.json(
+          { error: "You already have a booking for this pet at that date and time." },
+          409
+        );
+      }
+      throw err;
+    }
 
     return c.json(entry, 201);
   }