Promote GRO-2294 to UAT: Route Optimization security hardening (#194)

Promote dev→uat: GRO-2225 + GRO-2235 + GRO-2157 (atomic)

QA-approved on 37e42b3. CI green (Test, Lint & Typecheck, Build & Push).

UAT_PLAYBOOK.md

@@ -133,6 +133,7 @@ Geocoding turns a client's street address into `latitude`/`longitude` + `geocode
 | TC-API-2.11 | Geocode endpoint is manager-only | As **groomer** or **receptionist**, `POST /api/clients/{id}/geocode` | 403 Forbidden (role not permitted) |
 | TC-API-2.12 | Batch geocode un-geocoded clients | As manager, `POST /api/clients/geocode-batch?limit=10` on a DB with un-geocoded clients | 200 OK; body `{ provider, processed, geocoded, unresolved, errors, remaining, outcomes[] }`. `processed` ≤ 10; `remaining` reflects un-geocoded clients beyond this batch. Re-run while `remaining > 0` to finish (throttled to provider rate limit) |
 | TC-API-2.13 | Batch geocode — invalid limit | As manager, `POST /api/clients/geocode-batch?limit=0` (or non-numeric) | 400 `{ error: "limit must be a positive integer" }` |
+| TC-API-2.13a | Batch geocode — `?limit` cap enforced (GRO-2294) | As manager, `POST /api/clients/geocode-batch?limit=100000` on a DB with un-geocoded clients | 200 OK; the request is **clamped to the documented max of 500** — `processed` ≤ 500 (never the raw 100000). A fractional `?limit` (e.g. `49.9`) is floored to `49`. Confirms a manager cannot hold one synchronous request open / accrue unbounded Google API cost via an oversized limit |
 | TC-API-2.14 | Batch geocode — manager-only | As groomer/receptionist, `POST /api/clients/geocode-batch` | 403 Forbidden |
 | TC-API-2.15 | Auto-geocode on create | As manager/receptionist, `POST /api/clients` with a valid `address` | 201 Created; response includes a `geocoding` object (`status: "geocoded"` for a resolvable address) and the persisted client carries `latitude`/`longitude`/`geocodedAt`. Creating without an address succeeds with no `geocoding` field |
 | TC-API-2.16 | Auto-geocode on address update | As manager/receptionist, `PATCH /api/clients/{id}` changing `address` to a new valid value | 200 OK; response includes a `geocoding` object and refreshed coordinates. Patching unrelated fields (e.g. `name`) does NOT re-geocode (no `geocoding` field) |
@@ -165,6 +166,8 @@ 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"}` |
@@ -281,6 +284,9 @@ This means:
 | TC-API-8.13 | Portal pet update — owner success + persistence (GRO-2187, fixes [GRO-1480](/GRO/issues/GRO-1480) §5.23) | With a portal session for the pet's owner, `PATCH /api/portal/pets/{petId}` with body `{ "name": "...", "breed": "...", "weightKg": 18.25, "healthAlerts": "...", "coatType": "double", "petSizeCategory": "xlarge", "preferredCuts": ["teddy bear"], "medicalAlerts": [{"type":"allergy","description":"oatmeal","severity":"medium"}] }` | 200 OK; response reflects the update with `petSizeCategory: "extra_large"` (web `xlarge` → DB `extra_large`). A follow-up `GET /api/portal/pets` shows the persisted values |
 | 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
 
@@ -326,7 +332,7 @@ This means:
 
 | # | Scenario | Steps | Expected |
 |---|----------|-------|----------|
-| TC-API-13.1 | Get business settings | GET /api/admin/settings | 200 OK, business settings returned |
+| TC-API-13.1 | Get business settings | GET /api/admin/settings | 200 OK, business settings returned. Response body **must NOT include `googleMapsApiKey`** — the encrypted secret is redacted from the projection (GRO-2294, defense-in-depth); non-secret fields (`businessName`, colors, `routeOptimizationProvider`, etc.) are still present |
 | TC-API-13.2 | Update business settings | PATCH /api/admin/settings with updated values | 200 OK, settings updated |
 | TC-API-13.3 | Upload logo | POST /api/admin/settings/logo/upload with file | 200 OK, logo uploaded and stored |
 | TC-API-13.4 | View logo | GET /api/admin/settings/logo | 200 OK, logo image returned |
@@ -358,6 +364,74 @@ This means:
 | TC-API-15.6 | Reject missing required fields | POST /api/admin/buffer-rules with service only | 400 Bad Request, species and sizeCategory required |
 | TC-API-15.7 | Booking uses buffer | Book appointment for pet with sizeCategory; verify duration reflects buffer | 201 Created, appointment duration includes buffer time |
 
+### 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 (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 |
+|---|----------|-------|----------|
+| TC-API-16.1 | Fetch daily route (auto-create draft) | As **manager**, `GET /api/routes/daily?staffId={groomerId}&date=YYYY-MM-DD` for a date with no existing route | 200 OK; body `{ route, stops }`. `route.status` is `"draft"`, `route.staffId`/`routeDate` match, `stops` is `[]`. Re-calling returns the same route row (no duplicate) |
+| TC-API-16.2 | Optimize a multi-stop day | As manager, with ≥2 geocoded appointments for the groomer on the date, `POST /api/routes/optimize` body `{ "staffId": "{groomerId}", "date": "YYYY-MM-DD" }` | 200 OK; `route.status: "optimized"`, `optimizedAt` set, `totalTravelMins`/`totalDistanceKm` populated. `stops` ordered by `stopOrder` (1..N); first stop has `travelMinsFromPrev: null`, the rest positive. `provider` is `"nearest_neighbor"` (no Google key in UAT). The first stop carries `bufferMins: 0` (no predecessor); every later stop carries `bufferMins` = `businessSettings.defaultTravelBufferMins` (default 15). Response also includes `hasConflicts` / `conflictCount` and each stop a `conflict` object (GRO-2156, see §4.17) |
+| TC-API-16.3 | Re-optimize replaces prior order | As manager, run TC-API-16.2 twice | Second call returns 200; stops fully replaced (no duplicate `route_stops`, `stopOrder` still contiguous 1..N), `optimizedAt` refreshed |
+| TC-API-16.4 | Skips un-geocoded appointments | As manager, optimize a day where one appointment's client has no coordinates | 200 OK; that appointment is absent from `stops` and listed under `skipped[]` with `reason: "client address is not geocoded"`; a corresponding entry appears in `warnings[]` |
+| TC-API-16.5 | Empty / single-stop day | As manager, optimize a date with 0 (or 1) geocoded appointments | 200 OK; `route.status: "optimized"`, `totalTravelMins: 0`, `totalDistanceKm: "0.00"`. For 1 stop, `stops` has one entry with `travelMinsFromPrev: null` |
+| TC-API-16.6 | >25 stops chunked with warning | As manager, optimize a day with >25 geocoded appointments | 200 OK; `chunked: true`, `subRouteCount ≥ 2`, a `warnings[]` entry mentions sub-routes; all appointments appear exactly once with contiguous `stopOrder` |
+| TC-API-16.7 | Groomer reads own route | As **groomer**, `GET /api/routes/daily?date=YYYY-MM-DD` (omit staffId, or pass own id) | 200 OK; route resolves to the groomer's own `staffId` |
+| TC-API-16.8 | Groomer cannot access another's route | As groomer, `GET /api/routes/daily?staffId={otherGroomerId}&date=...` or `POST /api/routes/optimize` with another `staffId` | 403 Forbidden (`groomers may only access their own route`) |
+| TC-API-16.9 | Receptionist denied | As **receptionist**, `GET /api/routes/daily?...` or `POST /api/routes/optimize` | 403 Forbidden (role not permitted) |
+| TC-API-16.10 | Manager must supply staffId | As manager, `POST /api/routes/optimize` body `{ "date": "YYYY-MM-DD" }` (no staffId) | 400 `{ error: "staffId is required" }` |
+| TC-API-16.11 | Invalid date rejected | `GET /api/routes/daily?staffId=...&date=06-08-2026` (wrong format) | 400 validation error (`date must be YYYY-MM-DD`) |
+
+### 4.17 Route Optimization — Travel Buffer + Reorder (GRO-2156, Phase 2.2)
+
+Builds on §4.16. After optimization each consecutive leg carries a travel `bufferMins` (= `businessSettings.defaultTravelBufferMins`, default 15; the first stop is `0`). The API derives a per-stop **`conflict`** object at read time on `GET /api/routes/daily`, `POST /api/routes/optimize`, and `PATCH /api/routes/:routeId/reorder`:
+
+- `conflict.scheduleGapMins` — minutes between the previous appointment's `endTime` and this appointment's `startTime` (null for the first stop)
+- `conflict.requiredGapMins` — `travelMinsFromPrev + bufferMins` (null for the first stop)
+- `conflict.shortfallMins` — `requiredGapMins − scheduleGapMins` (positive ⇒ tight)
+- `conflict.hasConflict` — true when `shortfallMins > 0` ("tight schedule"); appointments are **never auto-moved**, only flagged
+
+`PATCH /api/routes/:routeId/reorder` accepts `{ "stopOrder": ["<routeStopId>", …] }` (every current stop id, exactly once, first-to-last), persists the new `stopOrder`, re-estimates each leg's travel offline for the new adjacency, re-applies buffers, recomputes route totals, and returns the route with refreshed conflict flags. **Auth: manager (any route) or groomer (own route only).**
+
+| ID | Scenario | Steps | Expected |
+|----|----------|-------|----------|
+| TC-API-17.1 | Conflict flags on optimize | As manager, optimize a day with ≥2 geocoded appointments whose times are close together | 200 OK; top-level `hasConflicts` (bool) + `conflictCount` (int). First stop `conflict.hasConflict:false` with null gap fields. A later stop whose `scheduleGapMins < travelMinsFromPrev + bufferMins` has `conflict.hasConflict:true` and positive `shortfallMins` |
+| TC-API-17.2 | No false conflict on a roomy schedule | Optimize a day where appointment gaps comfortably exceed travel + buffer | 200 OK; `hasConflicts:false`, `conflictCount:0`, every `conflict.shortfallMins ≤ 0` |
+| TC-API-17.3 | Reorder persists new order | As manager, take an optimized route, `PATCH /api/routes/{routeId}/reorder` with the stop ids in a new order | 200 OK; `stops` returned in the requested order with contiguous `stopOrder` 1..N; first stop `travelMinsFromPrev:null`/`bufferMins:0`, others recomputed; `route.totalTravelMins`/`totalDistanceKm` updated |
+| TC-API-17.4 | Reorder re-flags conflicts | Reorder so a far-apart pair becomes adjacent | 200 OK; `conflict` flags recomputed for the new adjacency (`hasConflicts`/`conflictCount` reflect the new order) |
+| TC-API-17.5 | Reorder validation — wrong stop set | `PATCH …/reorder` with a missing, extra, duplicate, or unknown stop id | 400 with an explanatory `error` (e.g. "must list every stop exactly once", "unknown stop id", "duplicate stop id") |
+| TC-API-17.6 | Reorder unknown route | `PATCH /api/routes/{randomUuid}/reorder` with any body | 404 `{ error: "Route not found" }` |
+| TC-API-17.7 | Reorder invalid routeId | `PATCH /api/routes/not-a-uuid/reorder` | 400 `{ error: "routeId must be a UUID" }` |
+| TC-API-17.8 | Groomer cannot reorder another's route | As groomer, reorder a route owned by a different groomer | 403 Forbidden (`groomers may only access their own route`) |
+
+### 4.18 Route Optimization — Navigation Export (GRO-2157, Phase 2.3)
+
+Builds on §4.16/§4.17. Two read-only endpoints turn an optimized route into a native-navigation deep-link URL the frontend opens on the groomer's phone:
+
+- `GET /api/routes/:routeId/export/google-maps` → Google Maps URLs API link (`https://www.google.com/maps/dir/?api=1&travelmode=driving&origin=…&destination=…&waypoints=…`)
+- `GET /api/routes/:routeId/export/apple-maps` → Apple Maps URL scheme (`maps://?saddr=…&daddr=<first>+to:<next>…&dirflg=d`)
+
+Both use the stops' stored `latitude`/`longitude` in `stopOrder`: **origin = first stop, destination = last stop, the rest are ordered intermediate waypoints**. Each response body is `{ platform, url, stopCount, waypointCount }` where `waypointCount` = stops minus origin and destination. Waypoint limits are validated per platform: **Google Maps ≤ 9**, **Apple Maps ≤ 15** intermediate waypoints; over-limit routes return 400. **Auth: manager (any route) or groomer (own route only); receptionists have no access.**
+
+| ID | Scenario | Steps | Expected |
+|----|----------|-------|----------|
+| TC-API-18.1 | Google Maps export of a multi-stop route | As manager, optimize a multi-stop day (§4.16), then `GET /api/routes/{routeId}/export/google-maps` | 200 OK; `platform:"google-maps"`, `url` starts `https://www.google.com/maps/dir/?api=1`, contains `travelmode=driving`, `origin`/`destination` are the first/last stop coords, `waypoints` lists the middle stops in order (pipe-separated). `stopCount` = total stops, `waypointCount` = `stopCount − 2` |
+| TC-API-18.2 | Apple Maps export of a multi-stop route | As manager, `GET /api/routes/{routeId}/export/apple-maps` for the same route | 200 OK; `platform:"apple-maps"`, `url` starts `maps://?saddr=`, `daddr` chains the remaining stops with `+to:`, ends `&dirflg=d`; `stopCount`/`waypointCount` as above |
+| TC-API-18.3 | Single-stop route | Export a route (google-maps and apple-maps) that has exactly one stop | 200 OK; `waypointCount:0`. Google url has `destination` and no `waypoints=`; Apple url is `maps://?daddr=<coord>&dirflg=d` (no `saddr`) |
+| TC-API-18.4 | Empty route rejected | Export a route with no stops (a fresh `draft` route) | 400 `{ error: "route has no stops to export" }` |
+| TC-API-18.5 | Google waypoint limit | Export (google-maps) a route with >11 stops (>9 intermediate waypoints) | 400 with an `error` mentioning Google Maps' limit of 9 |
+| TC-API-18.6 | Apple waypoint limit | Export (apple-maps) a route with >17 stops (>15 intermediate waypoints) | 400 with an `error` mentioning Apple Maps' limit of 15 |
+| TC-API-18.7 | Unknown route | `GET /api/routes/{randomUuid}/export/google-maps` | 404 `{ error: "Route not found" }` |
+| TC-API-18.8 | Invalid routeId | `GET /api/routes/not-a-uuid/export/apple-maps` | 400 `{ error: "routeId must be a UUID" }` |
+| TC-API-18.9 | Groomer exports own route | As **groomer**, export a route owned by self | 200 OK; deep-link returned |
+| TC-API-18.10 | Groomer cannot export another's route | As groomer, export a route owned by a different groomer | 403 Forbidden (`groomers may only access their own route`) |
+| TC-API-18.11 | Receptionist denied | As **receptionist**, export any route | 403 Forbidden (role not permitted) |
+
 ## Pass/Fail Criteria
 
 **Pass:**

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__/geocodeBatchLimit.test.ts

@@ -0,0 +1,89 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { Hono } from "hono";
+
+// ─── Mocks ──────────────────────────────────────────────────────────────────
+// GRO-2294: the POST /clients/geocode-batch handler must clamp ?limit to the
+// documented maximum (500) before invoking the geocoding service. We mock the
+// service to capture the exact limit the route forwards.
+
+const geocodeUngeocodedClients = vi.fn(async () => ({
+  totalRemaining: 0,
+  processed: 0,
+  geocoded: 0,
+  failed: 0,
+  remaining: 0,
+}));
+
+vi.mock("../services/clientGeocoding.js", () => ({
+  geocodeUngeocodedClients,
+  geocodeClient: vi.fn(),
+  resolveClientGeocodingProvider: vi.fn(),
+}));
+
+vi.mock("@groombook/db", () => {
+  const tableProxy = (name: string) =>
+    new Proxy(
+      { _name: name },
+      { get: (_t, p) => (p === "_name" ? name : { table: name, column: p }) }
+    );
+  return {
+    getDb: () => ({}),
+    clients: tableProxy("clients"),
+    appointments: tableProxy("appointments"),
+    and: vi.fn(),
+    eq: vi.fn(),
+    or: vi.fn(),
+    exists: vi.fn(),
+  };
+});
+
+const { clientsRouter } = await import("../routes/clients.js");
+
+const app = new Hono();
+app.route("/clients", clientsRouter);
+
+function postBatch(query: string) {
+  return app.request(`/clients/geocode-batch${query}`, { method: "POST" });
+}
+
+describe("POST /clients/geocode-batch — ?limit cap (GRO-2294)", () => {
+  beforeEach(() => {
+    geocodeUngeocodedClients.mockClear();
+  });
+
+  it("defaults to 50 when no ?limit is supplied", async () => {
+    const res = await postBatch("");
+    expect(res.status).toBe(200);
+    expect(geocodeUngeocodedClients).toHaveBeenCalledWith(expect.anything(), 50);
+  });
+
+  it("passes through a value within the cap", async () => {
+    const res = await postBatch("?limit=120");
+    expect(res.status).toBe(200);
+    expect(geocodeUngeocodedClients).toHaveBeenCalledWith(expect.anything(), 120);
+  });
+
+  it("clamps an over-cap value to 500", async () => {
+    const res = await postBatch("?limit=100000");
+    expect(res.status).toBe(200);
+    expect(geocodeUngeocodedClients).toHaveBeenCalledWith(expect.anything(), 500);
+  });
+
+  it("floors a fractional value before clamping", async () => {
+    const res = await postBatch("?limit=49.9");
+    expect(res.status).toBe(200);
+    expect(geocodeUngeocodedClients).toHaveBeenCalledWith(expect.anything(), 49);
+  });
+
+  it("rejects a non-positive limit with 400", async () => {
+    const res = await postBatch("?limit=0");
+    expect(res.status).toBe(400);
+    expect(geocodeUngeocodedClients).not.toHaveBeenCalled();
+  });
+
+  it("rejects a non-numeric limit with 400", async () => {
+    const res = await postBatch("?limit=abc");
+    expect(res.status).toBe(400);
+    expect(geocodeUngeocodedClients).not.toHaveBeenCalled();
+  });
+});

src/__tests__/navigationExport.test.ts

@@ -0,0 +1,140 @@
+import { describe, it, expect } from "vitest";
+import {
+  buildGoogleMapsUrl,
+  buildAppleMapsUrl,
+  buildNavigationUrl,
+  intermediateWaypointCount,
+  GOOGLE_MAPS_MAX_WAYPOINTS,
+  APPLE_MAPS_MAX_WAYPOINTS,
+  type NavigationStop,
+} from "../services/navigationExport.js";
+
+function stops(n: number): NavigationStop[] {
+  return Array.from({ length: n }, (_, i) => ({
+    latitude: 47 + i / 100,
+    longitude: -122 - i / 100,
+    label: `Stop ${i + 1}`,
+  }));
+}
+
+describe("intermediateWaypointCount", () => {
+  it("excludes origin and destination", () => {
+    expect(intermediateWaypointCount(0)).toBe(0);
+    expect(intermediateWaypointCount(1)).toBe(0);
+    expect(intermediateWaypointCount(2)).toBe(0);
+    expect(intermediateWaypointCount(5)).toBe(3);
+  });
+});
+
+describe("buildGoogleMapsUrl", () => {
+  it("rejects an empty route", () => {
+    const r = buildGoogleMapsUrl([]);
+    expect(r).toEqual({ error: "route has no stops to export", status: 400 });
+  });
+
+  it("builds a single-stop link (destination only, no waypoints)", () => {
+    const r = buildGoogleMapsUrl(stops(1));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.platform).toBe("google-maps");
+    expect(r.stopCount).toBe(1);
+    expect(r.waypointCount).toBe(0);
+    expect(r.url).toContain("https://www.google.com/maps/dir/?");
+    expect(r.url).toContain("api=1");
+    expect(r.url).toContain("travelmode=driving");
+    expect(r.url).toContain("origin=47%2C-122");
+    expect(r.url).toContain("destination=47%2C-122");
+    expect(r.url).not.toContain("waypoints=");
+  });
+
+  it("builds origin/destination only for two stops", () => {
+    const r = buildGoogleMapsUrl(stops(2));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.waypointCount).toBe(0);
+    expect(r.url).not.toContain("waypoints=");
+    expect(r.url).toContain("origin=47%2C-122");
+    expect(r.url).toContain("destination=47.01%2C-122.01");
+  });
+
+  it("includes intermediate waypoints in order, pipe-separated", () => {
+    const r = buildGoogleMapsUrl(stops(4));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.stopCount).toBe(4);
+    expect(r.waypointCount).toBe(2);
+    // waypoints param holds stops[1] and stops[2], pipe-joined (encoded %7C)
+    const url = new URL(r.url);
+    expect(url.searchParams.get("origin")).toBe("47,-122");
+    expect(url.searchParams.get("destination")).toBe("47.03,-122.03");
+    expect(url.searchParams.get("waypoints")).toBe(
+      "47.01,-122.01|47.02,-122.02"
+    );
+  });
+
+  it("accepts a route at exactly the waypoint limit", () => {
+    const r = buildGoogleMapsUrl(stops(GOOGLE_MAPS_MAX_WAYPOINTS + 2));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.waypointCount).toBe(GOOGLE_MAPS_MAX_WAYPOINTS);
+  });
+
+  it("rejects a route over the waypoint limit", () => {
+    const r = buildGoogleMapsUrl(stops(GOOGLE_MAPS_MAX_WAYPOINTS + 3));
+    expect("error" in r).toBe(true);
+    if ("error" in r) {
+      expect(r.status).toBe(400);
+      expect(r.error).toContain(`${GOOGLE_MAPS_MAX_WAYPOINTS}`);
+    }
+  });
+});
+
+describe("buildAppleMapsUrl", () => {
+  it("rejects an empty route", () => {
+    const r = buildAppleMapsUrl([]);
+    expect(r).toEqual({ error: "route has no stops to export", status: 400 });
+  });
+
+  it("builds a destination-only link for one stop", () => {
+    const r = buildAppleMapsUrl(stops(1));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.platform).toBe("apple-maps");
+    expect(r.url).toBe("maps://?daddr=47,-122&dirflg=d");
+    expect(r.url).not.toContain("saddr=");
+  });
+
+  it("chains destinations with +to: for multiple stops", () => {
+    const r = buildAppleMapsUrl(stops(3));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.stopCount).toBe(3);
+    expect(r.waypointCount).toBe(1);
+    expect(r.url).toBe(
+      "maps://?saddr=47,-122&daddr=47.01,-122.01+to:47.02,-122.02&dirflg=d"
+    );
+  });
+
+  it("accepts a route at exactly the waypoint limit", () => {
+    const r = buildAppleMapsUrl(stops(APPLE_MAPS_MAX_WAYPOINTS + 2));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.waypointCount).toBe(APPLE_MAPS_MAX_WAYPOINTS);
+  });
+
+  it("rejects a route over the waypoint limit", () => {
+    const r = buildAppleMapsUrl(stops(APPLE_MAPS_MAX_WAYPOINTS + 3));
+    expect("error" in r).toBe(true);
+    if ("error" in r) {
+      expect(r.status).toBe(400);
+      expect(r.error).toContain(`${APPLE_MAPS_MAX_WAYPOINTS}`);
+    }
+  });
+});
+
+describe("buildNavigationUrl", () => {
+  it("dispatches to the google-maps builder", () => {
+    const r = buildNavigationUrl("google-maps", stops(2));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.platform).toBe("google-maps");
+  });
+
+  it("dispatches to the apple-maps builder", () => {
+    const r = buildNavigationUrl("apple-maps", stops(2));
+    if ("error" in r) throw new Error(r.error);
+    expect(r.platform).toBe("apple-maps");
+  });
+});

src/__tests__/portalPets.test.ts

@@ -280,6 +280,23 @@ describe("PATCH /portal/pets/:petId", () => {
     expect(res.status).toBe(404);
   });
 
+  it("returns 404 for a malformed (non-UUID) petId without hitting the db (GRO-2203)", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    // A non-UUID petId previously reached `where(eq(pets.id, ...))` and made
+    // Postgres throw "invalid input syntax for type uuid" → unhandled 500.
+    // It must now short-circuit to 404 before any select/update.
+    selectPetRow = PET;
+
+    const res = await jsonPatch(
+      `/portal/pets/not-a-uuid`,
+      { coatType: "short" },
+      { "X-Impersonation-Session-Id": SESSION_ID }
+    );
+
+    expect(res.status).toBe(404);
+    expect(updatedValues).toHaveLength(0);
+  });
+
   it("returns 422 for an invalid coatType", async () => {
     selectSessionRow = ACTIVE_SESSION;
     selectPetRow = PET;

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/__tests__/routeOptimization.test.ts

@@ -0,0 +1,335 @@
+import { describe, it, expect } from "vitest";
+import {
+  haversineKm,
+  estimateLeg,
+  nearestNeighborOrder,
+  optimizeRoute,
+  detectScheduleConflicts,
+  recomputeLegsForOrder,
+  MAX_STOPS_PER_ROUTE,
+  type RouteStopInput,
+} from "../services/routeOptimization.js";
+import type { FetchLike } from "../services/geocoding.js";
+
+/** Builds a fake fetch returning a single JSON body, recording called URLs. */
+function fakeFetch(
+  body: unknown,
+  init: { ok?: boolean; status?: number; statusText?: string } = {}
+): { fetchImpl: FetchLike; calls: string[] } {
+  const calls: string[] = [];
+  const fetchImpl: FetchLike = async (url) => {
+    calls.push(url);
+    return {
+      ok: init.ok ?? true,
+      status: init.status ?? 200,
+      statusText: init.statusText ?? "OK",
+      json: async () => body,
+    };
+  };
+  return { fetchImpl, calls };
+}
+
+function stop(appointmentId: string, lat: number, lng: number): RouteStopInput {
+  return { appointmentId, latitude: lat, longitude: lng };
+}
+
+describe("haversineKm", () => {
+  it("is zero for the same point", () => {
+    expect(haversineKm({ latitude: 40, longitude: -74 }, { latitude: 40, longitude: -74 })).toBe(0);
+  });
+
+  it("approximates 1 degree of latitude as ~111km", () => {
+    const d = haversineKm({ latitude: 0, longitude: 0 }, { latitude: 1, longitude: 0 });
+    expect(d).toBeGreaterThan(110);
+    expect(d).toBeLessThan(112);
+  });
+});
+
+describe("estimateLeg", () => {
+  it("applies the circuity factor and average speed", () => {
+    const a = { latitude: 0, longitude: 0 };
+    const b = { latitude: 0, longitude: 1 };
+    const { distanceKm, mins } = estimateLeg(a, b);
+    // ~111km straight * 1.3 circuity ≈ 144.6km; at 40km/h ≈ 217 min
+    expect(distanceKm).toBeGreaterThan(140);
+    expect(distanceKm).toBeLessThan(150);
+    expect(mins).toBeGreaterThan(200);
+    expect(mins).toBeLessThan(230);
+    expect(Number.isInteger(mins)).toBe(true);
+  });
+});
+
+describe("nearestNeighborOrder", () => {
+  it("returns trivial order for 0 or 1 points", () => {
+    expect(nearestNeighborOrder([])).toEqual([]);
+    expect(nearestNeighborOrder([{ latitude: 1, longitude: 1 }])).toEqual([0]);
+  });
+
+  it("greedily visits the nearest unvisited point", () => {
+    // Points on a line; scrambled input order.
+    const points = [
+      { latitude: 0, longitude: 0 }, // 0 (start)
+      { latitude: 0, longitude: 5 }, // 1 (far)
+      { latitude: 0, longitude: 1 }, // 2
+      { latitude: 0, longitude: 2 }, // 3
+    ];
+    expect(nearestNeighborOrder(points, 0)).toEqual([0, 2, 3, 1]);
+  });
+});
+
+describe("optimizeRoute — nearest-neighbor fallback (no API key)", () => {
+  it("returns an empty route for no stops", async () => {
+    const r = await optimizeRoute([]);
+    expect(r.stops).toHaveLength(0);
+    expect(r.totalTravelMins).toBe(0);
+    expect(r.totalDistanceKm).toBe(0);
+    expect(r.provider).toBe("nearest_neighbor");
+    expect(r.chunked).toBe(false);
+  });
+
+  it("handles a single stop with null travel-from-prev", async () => {
+    const r = await optimizeRoute([stop("a", 40, -74)]);
+    expect(r.stops).toHaveLength(1);
+    expect(r.stops[0]!.travelMinsFromPrev).toBeNull();
+    expect(r.stops[0]!.travelDistanceKmFromPrev).toBeNull();
+    expect(r.totalTravelMins).toBe(0);
+  });
+
+  it("orders multiple stops greedily and sums totals", async () => {
+    const stops = [
+      stop("start", 0, 0),
+      stop("far", 0, 5),
+      stop("near1", 0, 1),
+      stop("near2", 0, 2),
+    ];
+    const r = await optimizeRoute(stops);
+    expect(r.provider).toBe("nearest_neighbor");
+    expect(r.stops.map((s) => s.appointmentId)).toEqual([
+      "start",
+      "near1",
+      "near2",
+      "far",
+    ]);
+    // First stop has no inbound leg.
+    expect(r.stops[0]!.travelMinsFromPrev).toBeNull();
+    // Remaining stops have positive travel.
+    for (const s of r.stops.slice(1)) {
+      expect(s.travelMinsFromPrev!).toBeGreaterThan(0);
+      expect(s.travelDistanceKmFromPrev!).toBeGreaterThan(0);
+    }
+    const summed = r.stops.reduce((acc, s) => acc + (s.travelMinsFromPrev ?? 0), 0);
+    expect(r.totalTravelMins).toBe(summed);
+  });
+});
+
+describe("optimizeRoute — Google Directions path", () => {
+  it("uses optimized waypoint order and real leg metrics, dropping the return leg", async () => {
+    const stops = [stop("A", 0, 0), stop("B", 0, 1), stop("C", 0, 2)];
+    // waypoints = [B, C]; optimizer reorders them to [C, B] (waypoint_order [1,0]).
+    // legs: A->C, C->B, B->A(return). The return leg must be dropped.
+    const { fetchImpl, calls } = fakeFetch({
+      status: "OK",
+      routes: [
+        {
+          waypoint_order: [1, 0],
+          legs: [
+            { distance: { value: 2000 }, duration: { value: 600 } }, // A->C
+            { distance: { value: 1000 }, duration: { value: 300 } }, // C->B
+            { distance: { value: 3000 }, duration: { value: 900 } }, // B->A (return, dropped)
+          ],
+        },
+      ],
+    });
+
+    const r = await optimizeRoute(stops, { googleApiKey: "key", fetchImpl });
+    expect(r.provider).toBe("google");
+    expect(r.stops.map((s) => s.appointmentId)).toEqual(["A", "C", "B"]);
+    expect(r.stops[0]!.travelMinsFromPrev).toBeNull();
+    expect(r.stops[1]!.travelDistanceKmFromPrev).toBe(2); // 2000m -> 2km
+    expect(r.stops[1]!.travelMinsFromPrev).toBe(10); // 600s -> 10min
+    expect(r.stops[2]!.travelDistanceKmFromPrev).toBe(1); // 1000m
+    expect(r.stops[2]!.travelMinsFromPrev).toBe(5); // 300s
+    expect(r.totalDistanceKm).toBe(3);
+    expect(r.totalTravelMins).toBe(15);
+    expect(decodeURIComponent(calls[0]!)).toContain("optimize:true");
+  });
+
+  it("falls back to the heuristic when Google returns a non-OK status", async () => {
+    const stops = [stop("A", 0, 0), stop("B", 0, 1), stop("C", 0, 2)];
+    const { fetchImpl } = fakeFetch({ status: "REQUEST_DENIED", error_message: "bad key" });
+    const r = await optimizeRoute(stops, { googleApiKey: "key", fetchImpl });
+    // Provider label reflects the chosen strategy (google requested) but a
+    // warning records the degradation and stops are still ordered.
+    expect(r.stops).toHaveLength(3);
+    expect(r.warnings.some((w) => w.includes("offline heuristic"))).toBe(true);
+    expect(r.stops[0]!.travelMinsFromPrev).toBeNull();
+  });
+});
+
+describe("optimizeRoute — >25 stop chunking", () => {
+  it("splits into sub-routes with a warning and continuous stop ordering", async () => {
+    const stops: RouteStopInput[] = [];
+    for (let i = 0; i < MAX_STOPS_PER_ROUTE + 5; i++) {
+      stops.push(stop(`s${i}`, 0, i * 0.1));
+    }
+    const r = await optimizeRoute(stops);
+    expect(r.chunked).toBe(true);
+    expect(r.subRouteCount).toBe(2);
+    expect(r.warnings.some((w) => w.includes("sub-routes"))).toBe(true);
+    expect(r.stops).toHaveLength(MAX_STOPS_PER_ROUTE + 5);
+    // Only the very first stop of the whole route lacks an inbound leg.
+    expect(r.stops[0]!.travelMinsFromPrev).toBeNull();
+    expect(r.stops.slice(1).every((s) => s.travelMinsFromPrev !== null)).toBe(true);
+    // All appointment ids preserved exactly once.
+    expect(new Set(r.stops.map((s) => s.appointmentId)).size).toBe(stops.length);
+  });
+});
+
+describe("detectScheduleConflicts", () => {
+  const at = (iso: string) => new Date(iso);
+
+  it("returns no conflict and null gaps for an empty or single-stop route", () => {
+    expect(detectScheduleConflicts([])).toEqual([]);
+    const one = detectScheduleConflicts([
+      {
+        appointmentStartTime: at("2026-06-08T09:00:00Z"),
+        appointmentEndTime: at("2026-06-08T10:00:00Z"),
+        travelMinsFromPrev: null,
+        bufferMins: 15,
+      },
+    ]);
+    expect(one).toEqual([
+      {
+        hasConflict: false,
+        scheduleGapMins: null,
+        requiredGapMins: null,
+        shortfallMins: null,
+      },
+    ]);
+  });
+
+  it("flags a tight schedule when gap < travel + buffer", () => {
+    // Stop 1 ends 10:00, stop 2 starts 10:20 → 20min gap. Travel 15 + buffer 15
+    // = 30 required → shortfall 10 → conflict.
+    const flags = detectScheduleConflicts([
+      {
+        appointmentStartTime: at("2026-06-08T09:00:00Z"),
+        appointmentEndTime: at("2026-06-08T10:00:00Z"),
+        travelMinsFromPrev: null,
+        bufferMins: 0,
+      },
+      {
+        appointmentStartTime: at("2026-06-08T10:20:00Z"),
+        appointmentEndTime: at("2026-06-08T11:00:00Z"),
+        travelMinsFromPrev: 15,
+        bufferMins: 15,
+      },
+    ]);
+    expect(flags[0]!.hasConflict).toBe(false);
+    expect(flags[1]).toEqual({
+      hasConflict: true,
+      scheduleGapMins: 20,
+      requiredGapMins: 30,
+      shortfallMins: 10,
+    });
+  });
+
+  it("does not flag when the gap comfortably covers travel + buffer", () => {
+    // 90min gap, 15 travel + 15 buffer = 30 required → 60 slack → no conflict.
+    const flags = detectScheduleConflicts([
+      {
+        appointmentStartTime: at("2026-06-08T09:00:00Z"),
+        appointmentEndTime: at("2026-06-08T10:00:00Z"),
+        travelMinsFromPrev: null,
+        bufferMins: 0,
+      },
+      {
+        appointmentStartTime: at("2026-06-08T11:30:00Z"),
+        appointmentEndTime: at("2026-06-08T12:00:00Z"),
+        travelMinsFromPrev: 15,
+        bufferMins: 15,
+      },
+    ]);
+    expect(flags[1]).toEqual({
+      hasConflict: false,
+      scheduleGapMins: 90,
+      requiredGapMins: 30,
+      shortfallMins: -60,
+    });
+  });
+
+  it("treats a null travelMinsFromPrev as zero travel", () => {
+    const flags = detectScheduleConflicts([
+      {
+        appointmentStartTime: at("2026-06-08T09:00:00Z"),
+        appointmentEndTime: at("2026-06-08T10:00:00Z"),
+        travelMinsFromPrev: null,
+        bufferMins: 0,
+      },
+      {
+        appointmentStartTime: at("2026-06-08T10:05:00Z"),
+        appointmentEndTime: at("2026-06-08T11:00:00Z"),
+        travelMinsFromPrev: null,
+        bufferMins: 15,
+      },
+    ]);
+    // 5min gap vs 0 travel + 15 buffer = 15 required → conflict, shortfall 10.
+    expect(flags[1]!.hasConflict).toBe(true);
+    expect(flags[1]!.requiredGapMins).toBe(15);
+    expect(flags[1]!.shortfallMins).toBe(10);
+  });
+
+  it("flags overlapping appointments (negative gap) as conflicts", () => {
+    const flags = detectScheduleConflicts([
+      {
+        appointmentStartTime: at("2026-06-08T09:00:00Z"),
+        appointmentEndTime: at("2026-06-08T10:00:00Z"),
+        travelMinsFromPrev: null,
+        bufferMins: 0,
+      },
+      {
+        appointmentStartTime: at("2026-06-08T09:30:00Z"),
+        appointmentEndTime: at("2026-06-08T10:30:00Z"),
+        travelMinsFromPrev: 10,
+        bufferMins: 15,
+      },
+    ]);
+    expect(flags[1]!.scheduleGapMins).toBe(-30);
+    expect(flags[1]!.hasConflict).toBe(true);
+    expect(flags[1]!.shortfallMins).toBe(55);
+  });
+});
+
+describe("recomputeLegsForOrder", () => {
+  it("returns null travel for an empty or single-point order", () => {
+    expect(recomputeLegsForOrder([])).toEqual([]);
+    expect(recomputeLegsForOrder([{ latitude: 40, longitude: -74 }])).toEqual([
+      { travelMinsFromPrev: null, travelDistanceKmFromPrev: null },
+    ]);
+  });
+
+  it("estimates each leg for the fixed given order without reordering", () => {
+    const pts = [
+      { latitude: 0, longitude: 0 },
+      { latitude: 0, longitude: 1 },
+      { latitude: 0, longitude: 2 },
+    ];
+    const legs = recomputeLegsForOrder(pts);
+    expect(legs).toHaveLength(3);
+    expect(legs[0]).toEqual({
+      travelMinsFromPrev: null,
+      travelDistanceKmFromPrev: null,
+    });
+    // Each leg equals estimateLeg between adjacent points (no optimization).
+    const e01 = estimateLeg(pts[0]!, pts[1]!);
+    const e12 = estimateLeg(pts[1]!, pts[2]!);
+    expect(legs[1]).toEqual({
+      travelMinsFromPrev: e01.mins,
+      travelDistanceKmFromPrev: e01.distanceKm,
+    });
+    expect(legs[2]).toEqual({
+      travelMinsFromPrev: e12.mins,
+      travelDistanceKmFromPrev: e12.distanceKm,
+    });
+  });
+});

src/__tests__/settings.test.ts

@@ -0,0 +1,91 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { Hono } from "hono";
+
+// ─── Mocks ──────────────────────────────────────────────────────────────────
+// GRO-2294: GET /api/admin/settings must not return the encrypted
+// googleMapsApiKey ciphertext, on either the existing-row or auto-create branch.
+
+let selectRows: Record<string, unknown>[] = [];
+let insertReturning: Record<string, unknown>[] = [];
+
+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 passthrough
+      return target[prop];
+    },
+  });
+  return chain;
+}
+
+vi.mock("@groombook/db", () => {
+  const businessSettings = new Proxy(
+    { _name: "business_settings" },
+    { get: (_t, p) => (p === "_name" ? "business_settings" : { column: p }) }
+  );
+  return {
+    getDb: () => ({
+      select: () => ({ from: () => makeChainable(selectRows) }),
+      insert: () => ({
+        values: () => ({ returning: () => insertReturning }),
+      }),
+    }),
+    businessSettings,
+    eq: vi.fn(),
+  };
+});
+
+vi.mock("../lib/s3.js", () => ({
+  getPresignedUploadUrl: vi.fn(),
+  deleteObject: vi.fn(),
+  putObject: vi.fn(),
+  getObject: vi.fn(),
+}));
+
+const { settingsRouter } = await import("../routes/settings.js");
+
+const app = new Hono();
+app.route("/settings", settingsRouter);
+
+const FULL_ROW = {
+  id: "settings-uuid-1",
+  businessName: "GroomBook",
+  primaryColor: "#4f8a6f",
+  accentColor: "#8b7355",
+  routeOptimizationProvider: "google",
+  googleMapsApiKey: "ENCRYPTED::super-secret-ciphertext",
+  createdAt: new Date(),
+  updatedAt: new Date(),
+};
+
+describe("GET /settings — googleMapsApiKey redaction (GRO-2294)", () => {
+  beforeEach(() => {
+    selectRows = [];
+    insertReturning = [];
+  });
+
+  it("omits googleMapsApiKey from an existing settings row", async () => {
+    selectRows = [{ ...FULL_ROW }];
+    const res = await app.request("/settings", { method: "GET" });
+    expect(res.status).toBe(200);
+    const body = (await res.json()) as Record<string, unknown>;
+    expect(body).not.toHaveProperty("googleMapsApiKey");
+    // Non-secret fields are still returned.
+    expect(body.businessName).toBe("GroomBook");
+    expect(body.routeOptimizationProvider).toBe("google");
+  });
+
+  it("omits googleMapsApiKey from the auto-create branch", async () => {
+    selectRows = [];
+    insertReturning = [{ ...FULL_ROW, id: "settings-uuid-new" }];
+    const res = await app.request("/settings", { method: "GET" });
+    expect(res.status).toBe(200);
+    const body = (await res.json()) as Record<string, unknown>;
+    expect(body).not.toHaveProperty("googleMapsApiKey");
+    expect(body.id).toBe("settings-uuid-new");
+  });
+});

src/__tests__/waitlist.test.ts

@@ -184,6 +184,66 @@ describe("POST /portal/waitlist", () => {
     expect(insertedValues).toHaveLength(1);
   });
 
+  it("normalizes HH:MM:SS preferredTime and returns 201 (GRO-2211)", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    const res = await jsonRequest("POST", "/portal/waitlist", {
+      petId: VALID_UUID_3,
+      serviceId: VALID_UUID_4,
+      preferredDate: "2026-03-25",
+      preferredTime: "10:00:00",
+    }, { "X-Impersonation-Session-Id": VALID_UUID_5 });
+    expect(res.status).toBe(201);
+    expect(insertedValues[0]?.preferredTime).toBe("10:00:00");
+  });
+
+  it("normalizes HH:MM preferredTime to HH:MM:SS before insert (GRO-2211)", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    const res = await jsonRequest("POST", "/portal/waitlist", {
+      petId: VALID_UUID_3,
+      serviceId: VALID_UUID_4,
+      preferredDate: "2026-03-25",
+      preferredTime: "10:00",
+    }, { "X-Impersonation-Session-Id": VALID_UUID_5 });
+    expect(res.status).toBe(201);
+    expect(insertedValues[0]?.preferredTime).toBe("10:00:00");
+  });
+
+  it("returns 400 (not 500) for a full ISO datetime preferredTime (GRO-2211)", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    const res = await jsonRequest("POST", "/portal/waitlist", {
+      petId: VALID_UUID_3,
+      serviceId: VALID_UUID_4,
+      preferredDate: "2026-03-25",
+      preferredTime: "2026-06-09T10:00:00.000Z",
+    }, { "X-Impersonation-Session-Id": VALID_UUID_5 });
+    expect(res.status).toBe(400);
+    expect(insertedValues).toHaveLength(0);
+  });
+
+  it("returns 400 for a malformed preferredDate (GRO-2211)", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    const res = await jsonRequest("POST", "/portal/waitlist", {
+      petId: VALID_UUID_3,
+      serviceId: VALID_UUID_4,
+      preferredDate: "03/25/2026",
+      preferredTime: "10:00",
+    }, { "X-Impersonation-Session-Id": VALID_UUID_5 });
+    expect(res.status).toBe(400);
+    expect(insertedValues).toHaveLength(0);
+  });
+
+  it("returns 400 for an out-of-range preferredTime (GRO-2211)", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    const res = await jsonRequest("POST", "/portal/waitlist", {
+      petId: VALID_UUID_3,
+      serviceId: VALID_UUID_4,
+      preferredDate: "2026-03-25",
+      preferredTime: "25:99",
+    }, { "X-Impersonation-Session-Id": VALID_UUID_5 });
+    expect(res.status).toBe(400);
+    expect(insertedValues).toHaveLength(0);
+  });
+
   it("returns 401 without session", async () => {
     const res = await jsonRequest("POST", "/portal/waitlist", {
       petId: VALID_UUID_3,
@@ -258,6 +318,16 @@ describe("PATCH /portal/waitlist/:id", () => {
     expect(updatedValues[0]?.status).toBe("cancelled");
   });
 
+  it("returns 400 (not 500) for a full ISO datetime preferredTime on update (GRO-2211)", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    selectRows = [WAITLIST_ENTRY];
+    const res = await jsonRequest("PATCH", `/portal/waitlist/${VALID_UUID_1}`, {
+      preferredTime: "2026-06-09T10:00:00.000Z",
+    }, { "X-Impersonation-Session-Id": VALID_UUID_5 });
+    expect(res.status).toBe(400);
+    expect(updatedValues).toHaveLength(0);
+  });
+
   it("returns 401 without session", async () => {
     const res = await jsonRequest("PATCH", `/portal/waitlist/${VALID_UUID_1}`, {
       status: "cancelled",

src/index.ts

@@ -20,6 +20,7 @@ import { settingsRouter } from "./routes/settings.js";
 import { authProviderRouter } from "./routes/authProvider.js";
 import { searchRouter } from "./routes/search.js";
 import { bufferRulesRouter } from "./routes/buffer-rules.js";
+import { routesRouter } from "./routes/routes.js";
 import { getObject } from "./lib/s3.js";
 import { calendarRouter } from "./routes/calendar.js";
 import { setupRouter } from "./routes/setup.js";
@@ -220,6 +221,10 @@ api.use("/reports/*", requireRole("manager"));
 api.use("/invoices/*", requireRole("manager", "groomer"));
 api.use("/impersonation/*", requireRole("manager"));
 
+// Route optimization: manager (any groomer's route) or groomer (own route only,
+// enforced in-handler). Receptionists have no access. (GRO-2155)
+api.use("/routes/*", requireRole("manager", "groomer"));
+
 // Manager + Receptionist only (groomers have no access): appointment-groups, grooming-logs, waitlist
 api.use("/appointment-groups/*", requireRole("manager", "receptionist"));
 api.use("/grooming-logs/*", requireRole("manager", "receptionist"));
@@ -283,6 +288,7 @@ api.route("/admin/auth-provider", authProviderRouter);
 api.route("/admin/seed", adminSeedRouter);
 api.route("/search", searchRouter);
 api.route("/buffer-rules", bufferRulesRouter);
+api.route("/routes", routesRouter);
 
 const port = Number(process.env.PORT ?? 3000);
 await initAuth();

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/clients.ts

@@ -12,6 +12,12 @@ import {
 
 export const clientsRouter = new Hono<AppEnv>();
 
+// Batch-geocode bounds (GRO-2294): default 50, hard cap 500. The cap bounds how
+// long one synchronous request stays open and the per-request external API cost
+// when routeOptimizationProvider = "google".
+const GEOCODE_BATCH_DEFAULT_LIMIT = 50;
+const GEOCODE_BATCH_MAX_LIMIT = 500;
+
 type ClientRow = typeof clients.$inferSelect;
 
 /**
@@ -185,12 +191,15 @@ clientsRouter.post("/:clientId/geocode", async (c) => {
 clientsRouter.post("/geocode-batch", async (c) => {
   const db = getDb();
   const limitRaw = c.req.query("limit");
-  let limit = 50;
+  let limit = GEOCODE_BATCH_DEFAULT_LIMIT;
   if (limitRaw !== undefined) {
     limit = Number(limitRaw);
     if (!Number.isFinite(limit) || limit <= 0) {
       return c.json({ error: "limit must be a positive integer" }, 400);
     }
+    // Clamp to the documented maximum to bound synchronous request duration
+    // and (for the Google provider) per-request external API cost.
+    limit = Math.min(Math.floor(limit), GEOCODE_BATCH_MAX_LIMIT);
   }
   const summary = await geocodeUngeocodedClients(db, limit);
   return c.json(summary);

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();
 
@@ -296,6 +296,14 @@ portalRouter.patch(
     const body = c.req.valid("json");
     const clientId = c.get("portalClientId");
 
+    // GRO-2203: validate UUID format before hitting Postgres. Passing a non-UUID
+    // string to a uuid column makes the driver throw ("invalid input syntax for
+    // type uuid"), which previously surfaced as an unhandled 500. Mirror the
+    // GRO-2014 fix in pets.ts and treat a malformed id as Not found.
+    if (!z.string().uuid().safeParse(petId).success) {
+      return c.json({ error: "Not found" }, 404);
+    }
+
     const [pet] = await db
       .select()
       .from(pets)
@@ -551,17 +559,33 @@ portalRouter.post("/appointments/:id/cancel", async (c) => {
 
 // ─── Client-facing waitlist routes ────────────────────────────────────────────
 
+// Postgres `date` / `time` columns reject arbitrary strings (e.g. a full ISO
+// datetime), throwing a DateTimeParseError that surfaces as an unhandled 500.
+// Constrain client input here so malformed values are rejected with a 400 by
+// zValidator before they ever reach the DB (GRO-2211 defense-in-depth).
+const preferredDateSchema = z
+  .string()
+  .regex(/^\d{4}-\d{2}-\d{2}$/, "preferredDate must be YYYY-MM-DD");
+const preferredTimeSchema = z
+  .string()
+  .regex(/^([01]\d|2[0-3]):[0-5]\d(:[0-5]\d)?$/, "preferredTime must be HH:MM or HH:MM:SS");
+
+// Normalize HH:MM → HH:MM:SS so it matches the Postgres `time` column format.
+function normalizeTime(value: string): string {
+  return value.length === 5 ? `${value}:00` : value;
+}
+
 const createWaitlistEntrySchema = z.object({
   petId: z.string().uuid(),
   serviceId: z.string().uuid(),
-  preferredDate: z.string(),
-  preferredTime: z.string(),
+  preferredDate: preferredDateSchema,
+  preferredTime: preferredTimeSchema,
 });
 
 const updateWaitlistEntrySchema = z.object({
   status: z.literal("cancelled").optional(),
-  preferredDate: z.string().optional(),
-  preferredTime: z.string().optional(),
+  preferredDate: preferredDateSchema.optional(),
+  preferredTime: preferredTimeSchema.optional(),
 });
 
 portalRouter.post(
@@ -572,16 +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: 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);
   }
@@ -610,7 +650,7 @@ portalRouter.patch(
     const updateData: Record<string, unknown> = { updatedAt: new Date() };
     if (body.status !== undefined) updateData.status = body.status;
     if (body.preferredDate !== undefined) updateData.preferredDate = body.preferredDate;
-    if (body.preferredTime !== undefined) updateData.preferredTime = body.preferredTime;
+    if (body.preferredTime !== undefined) updateData.preferredTime = normalizeTime(body.preferredTime);
 
     const [updated] = await db
       .update(waitlistEntries)

src/routes/routes.ts

@@ -0,0 +1,529 @@
+import { Hono, type Context } from "hono";
+import { zValidator } from "@hono/zod-validator";
+import { z } from "zod/v3";
+import {
+  and,
+  asc,
+  eq,
+  gte,
+  lt,
+  ne,
+  getDb,
+  appointments,
+  businessSettings,
+  clients,
+  groomerRoutes,
+  routeStops,
+} from "@groombook/db";
+import type { AppEnv, StaffRow } from "../middleware/rbac.js";
+import {
+  optimizeRoute,
+  resolveRouteGoogleApiKey,
+  detectScheduleConflicts,
+  recomputeLegsForOrder,
+  type RouteStopInput,
+  type StopConflictFlags,
+} from "../services/routeOptimization.js";
+import {
+  buildNavigationUrl,
+  type NavigationPlatform,
+  type NavigationStop,
+} from "../services/navigationExport.js";
+
+export const routesRouter = new Hono<AppEnv>();
+
+const dailyQuerySchema = z.object({
+  staffId: z.string().uuid().optional(),
+  date: z.string().regex(/^\d{4}-\d{2}-\d{2}$/, "date must be YYYY-MM-DD"),
+});
+
+const optimizeBodySchema = z.object({
+  staffId: z.string().uuid().optional(),
+  date: z.string().regex(/^\d{4}-\d{2}-\d{2}$/, "date must be YYYY-MM-DD"),
+});
+
+const reorderBodySchema = z.object({
+  // New visiting order expressed as routeStops.id values, first-to-last.
+  stopOrder: z.array(z.string().uuid()).min(1),
+});
+
+/**
+ * Resolves the target staffId for the request and enforces the groomer-own /
+ * manager authorization rule. Groomers may only act on their own route; if a
+ * groomer omits staffId it defaults to their own. Returns either the resolved
+ * id or an error tuple the caller turns into a JSON response.
+ */
+function resolveTargetStaffId(
+  staffRow: StaffRow | undefined,
+  requestedStaffId: string | undefined
+): { staffId: string } | { error: string; status: 400 | 403 } {
+  const isGroomer = staffRow?.role === "groomer";
+
+  if (isGroomer) {
+    if (requestedStaffId && requestedStaffId !== staffRow.id) {
+      return {
+        error: "Forbidden: groomers may only access their own route",
+        status: 403,
+      };
+    }
+    return { staffId: staffRow.id };
+  }
+
+  // Manager: staffId is required (no implicit self — managers plan others' days).
+  if (!requestedStaffId) {
+    return { error: "staffId is required", status: 400 };
+  }
+  return { staffId: requestedStaffId };
+}
+
+/** Day window [date 00:00:00Z, nextDay 00:00:00Z) for filtering appointments. */
+function dayBounds(date: string): { start: Date; end: Date } {
+  const start = new Date(`${date}T00:00:00.000Z`);
+  const end = new Date(start.getTime() + 24 * 60 * 60 * 1000);
+  return { start, end };
+}
+
+/** Loads a route's persisted stops, enriched with appointment + client detail. */
+async function loadRouteStops(db: ReturnType<typeof getDb>, routeId: string) {
+  return db
+    .select({
+      id: routeStops.id,
+      appointmentId: routeStops.appointmentId,
+      stopOrder: routeStops.stopOrder,
+      latitude: routeStops.latitude,
+      longitude: routeStops.longitude,
+      travelMinsFromPrev: routeStops.travelMinsFromPrev,
+      travelDistanceKmFromPrev: routeStops.travelDistanceKmFromPrev,
+      bufferMins: routeStops.bufferMins,
+      appointmentStartTime: appointments.startTime,
+      appointmentEndTime: appointments.endTime,
+      appointmentStatus: appointments.status,
+      clientId: clients.id,
+      clientName: clients.name,
+      clientAddress: clients.address,
+    })
+    .from(routeStops)
+    .innerJoin(appointments, eq(routeStops.appointmentId, appointments.id))
+    .innerJoin(clients, eq(appointments.clientId, clients.id))
+    .where(eq(routeStops.routeId, routeId))
+    .orderBy(asc(routeStops.stopOrder));
+}
+
+type LoadedRouteStop = Awaited<ReturnType<typeof loadRouteStops>>[number];
+
+/**
+ * Annotates persisted stops with "tight schedule" conflict flags for the
+ * frontend. Conflicts are derived at read time from the live appointment times,
+ * persisted travel estimates and buffers — never auto-resolved by moving stops.
+ */
+function annotateConflicts(stops: LoadedRouteStop[]): {
+  stops: Array<LoadedRouteStop & { conflict: StopConflictFlags }>;
+  hasConflicts: boolean;
+  conflictCount: number;
+} {
+  const flags = detectScheduleConflicts(
+    stops.map((s) => ({
+      appointmentStartTime: s.appointmentStartTime,
+      appointmentEndTime: s.appointmentEndTime,
+      travelMinsFromPrev: s.travelMinsFromPrev,
+      bufferMins: s.bufferMins,
+    }))
+  );
+  const annotated = stops.map((s, i) => ({ ...s, conflict: flags[i]! }));
+  const conflictCount = flags.filter((f) => f.hasConflict).length;
+  return { stops: annotated, hasConflicts: conflictCount > 0, conflictCount };
+}
+
+/**
+ * GET /api/routes/daily?staffId=&date=
+ * Fetches (creating a draft if absent) the daily route for a groomer, with all
+ * persisted stops. Auth: groomer (own) or manager.
+ */
+routesRouter.get("/daily", zValidator("query", dailyQuerySchema), async (c) => {
+  const db = getDb();
+  const { staffId: requestedStaffId, date } = c.req.valid("query");
+
+  const resolved = resolveTargetStaffId(c.get("staff"), requestedStaffId);
+  if ("error" in resolved) {
+    return c.json({ error: resolved.error }, resolved.status);
+  }
+  const staffId = resolved.staffId;
+
+  let [route] = await db
+    .select()
+    .from(groomerRoutes)
+    .where(
+      and(
+        eq(groomerRoutes.staffId, staffId),
+        eq(groomerRoutes.routeDate, date)
+      )
+    );
+
+  if (!route) {
+    // Create a draft route so the day is addressable before optimization.
+    [route] = await db
+      .insert(groomerRoutes)
+      .values({ staffId, routeDate: date, status: "draft" })
+      .returning();
+  }
+
+  const stops = await loadRouteStops(db, route!.id);
+  const annotated = annotateConflicts(stops);
+  return c.json({
+    route,
+    stops: annotated.stops,
+    hasConflicts: annotated.hasConflicts,
+    conflictCount: annotated.conflictCount,
+  });
+});
+
+/**
+ * POST /api/routes/optimize  { staffId, date }
+ * Generates or re-optimizes the daily route: pulls the day's geocoded
+ * appointments, optimizes the visiting order (Google Directions when a key is
+ * configured, else nearest-neighbor), and persists the ordered stops + totals.
+ * Auth: groomer (own) or manager.
+ */
+routesRouter.post(
+  "/optimize",
+  zValidator("json", optimizeBodySchema),
+  async (c) => {
+    const db = getDb();
+    const { staffId: requestedStaffId, date } = c.req.valid("json");
+
+    const resolved = resolveTargetStaffId(c.get("staff"), requestedStaffId);
+    if ("error" in resolved) {
+      return c.json({ error: resolved.error }, resolved.status);
+    }
+    const staffId = resolved.staffId;
+    const { start, end } = dayBounds(date);
+
+    // Pull the day's non-cancelled appointments for this groomer, joined to the
+    // client coordinates. Ordered by start time so the earliest booking anchors
+    // the route.
+    const dayAppointments = await db
+      .select({
+        appointmentId: appointments.id,
+        startTime: appointments.startTime,
+        clientId: clients.id,
+        clientName: clients.name,
+        latitude: clients.latitude,
+        longitude: clients.longitude,
+      })
+      .from(appointments)
+      .innerJoin(clients, eq(appointments.clientId, clients.id))
+      .where(
+        and(
+          eq(appointments.staffId, staffId),
+          gte(appointments.startTime, start),
+          lt(appointments.startTime, end),
+          ne(appointments.status, "cancelled")
+        )
+      )
+      .orderBy(asc(appointments.startTime));
+
+    const stopInputs: RouteStopInput[] = [];
+    const skipped: Array<{ appointmentId: string; clientName: string; reason: string }> =
+      [];
+    for (const appt of dayAppointments) {
+      if (appt.latitude == null || appt.longitude == null) {
+        skipped.push({
+          appointmentId: appt.appointmentId,
+          clientName: appt.clientName,
+          reason: "client address is not geocoded",
+        });
+        continue;
+      }
+      stopInputs.push({
+        appointmentId: appt.appointmentId,
+        latitude: appt.latitude,
+        longitude: appt.longitude,
+      });
+    }
+
+    const [settings] = await db.select().from(businessSettings).limit(1);
+    const bufferMins = settings?.defaultTravelBufferMins ?? 15;
+
+    const googleApiKey = await resolveRouteGoogleApiKey(db);
+    const optimized = await optimizeRoute(stopInputs, { googleApiKey });
+
+    const warnings = [...optimized.warnings];
+    if (skipped.length > 0) {
+      warnings.push(
+        `${skipped.length} appointment(s) were skipped because the client address is not geocoded.`
+      );
+    }
+
+    const now = new Date();
+    const route = await db.transaction(async (tx) => {
+      // Upsert the route row for (staffId, date).
+      const [existing] = await tx
+        .select()
+        .from(groomerRoutes)
+        .where(
+          and(
+            eq(groomerRoutes.staffId, staffId),
+            eq(groomerRoutes.routeDate, date)
+          )
+        );
+
+      const [routeRow] = existing
+        ? await tx
+            .update(groomerRoutes)
+            .set({
+              status: "optimized",
+              totalTravelMins: optimized.totalTravelMins,
+              totalDistanceKm: optimized.totalDistanceKm.toFixed(2),
+              optimizedAt: now,
+              updatedAt: now,
+            })
+            .where(eq(groomerRoutes.id, existing.id))
+            .returning()
+        : await tx
+            .insert(groomerRoutes)
+            .values({
+              staffId,
+              routeDate: date,
+              status: "optimized",
+              totalTravelMins: optimized.totalTravelMins,
+              totalDistanceKm: optimized.totalDistanceKm.toFixed(2),
+              optimizedAt: now,
+            })
+            .returning();
+
+      // Replace stops: clear prior ordering, insert the freshly optimized one.
+      await tx.delete(routeStops).where(eq(routeStops.routeId, routeRow!.id));
+      if (optimized.stops.length > 0) {
+        await tx.insert(routeStops).values(
+          optimized.stops.map((s, i) => ({
+            routeId: routeRow!.id,
+            appointmentId: s.appointmentId,
+            stopOrder: i + 1,
+            latitude: s.latitude,
+            longitude: s.longitude,
+            travelMinsFromPrev: s.travelMinsFromPrev,
+            travelDistanceKmFromPrev:
+              s.travelDistanceKmFromPrev == null
+                ? null
+                : s.travelDistanceKmFromPrev.toFixed(2),
+            // Buffer applies between consecutive stops; the first stop has no
+            // predecessor, so it carries no travel buffer.
+            bufferMins: i === 0 ? 0 : bufferMins,
+          }))
+        );
+      }
+
+      return routeRow!;
+    });
+
+    const stops = await loadRouteStops(db, route.id);
+    const annotated = annotateConflicts(stops);
+    return c.json({
+      route,
+      stops: annotated.stops,
+      hasConflicts: annotated.hasConflicts,
+      conflictCount: annotated.conflictCount,
+      provider: optimized.provider,
+      chunked: optimized.chunked,
+      subRouteCount: optimized.subRouteCount,
+      skipped,
+      warnings,
+    });
+  }
+);
+
+/**
+ * PATCH /api/routes/:routeId/reorder  { stopOrder: string[] }
+ * Persists a manual stop order (array of routeStops.id, first-to-last), then
+ * re-runs the buffer logic: each leg's travel is re-estimated for the new
+ * adjacency, the default travel buffer is re-applied between consecutive stops,
+ * route totals are recomputed, and tight-schedule conflicts are re-flagged.
+ * Appointments are never moved. Auth: groomer (own route) or manager.
+ */
+routesRouter.patch(
+  "/:routeId/reorder",
+  zValidator("json", reorderBodySchema),
+  async (c) => {
+    const db = getDb();
+    const routeId = c.req.param("routeId");
+    if (!z.string().uuid().safeParse(routeId).success) {
+      return c.json({ error: "routeId must be a UUID" }, 400);
+    }
+    const { stopOrder: newOrderIds } = c.req.valid("json");
+
+    const [route] = await db
+      .select()
+      .from(groomerRoutes)
+      .where(eq(groomerRoutes.id, routeId));
+    if (!route) {
+      return c.json({ error: "Route not found" }, 404);
+    }
+
+    // Reuse the groomer-own / manager authorization rule against the route owner.
+    const resolved = resolveTargetStaffId(c.get("staff"), route.staffId);
+    if ("error" in resolved) {
+      return c.json({ error: resolved.error }, resolved.status);
+    }
+
+    const existing = await db
+      .select({
+        id: routeStops.id,
+        latitude: routeStops.latitude,
+        longitude: routeStops.longitude,
+      })
+      .from(routeStops)
+      .where(eq(routeStops.routeId, routeId));
+
+    // The new order must be an exact permutation of the route's current stops.
+    const existingIds = new Set(existing.map((s) => s.id));
+    if (newOrderIds.length !== existing.length) {
+      return c.json(
+        {
+          error: `stopOrder must list every stop exactly once (expected ${existing.length}, got ${newOrderIds.length})`,
+        },
+        400
+      );
+    }
+    const seen = new Set<string>();
+    for (const id of newOrderIds) {
+      if (!existingIds.has(id)) {
+        return c.json({ error: `unknown stop id: ${id}` }, 400);
+      }
+      if (seen.has(id)) {
+        return c.json({ error: `duplicate stop id: ${id}` }, 400);
+      }
+      seen.add(id);
+    }
+
+    const [settings] = await db.select().from(businessSettings).limit(1);
+    const bufferMins = settings?.defaultTravelBufferMins ?? 15;
+
+    const byId = new Map(existing.map((s) => [s.id, s]));
+    const legs = recomputeLegsForOrder(
+      newOrderIds.map((id) => {
+        const s = byId.get(id)!;
+        return { latitude: s.latitude, longitude: s.longitude };
+      })
+    );
+
+    const totalTravelMins = legs.reduce(
+      (sum, l) => sum + (l.travelMinsFromPrev ?? 0),
+      0
+    );
+    const totalDistanceKm =
+      Math.round(
+        legs.reduce((sum, l) => sum + (l.travelDistanceKmFromPrev ?? 0), 0) * 100
+      ) / 100;
+
+    const now = new Date();
+    await db.transaction(async (tx) => {
+      // Two-pass update: park stopOrder in a non-colliding negative range first
+      // so the unique(routeId, stopOrder) constraint never trips mid-reorder.
+      for (let i = 0; i < newOrderIds.length; i++) {
+        await tx
+          .update(routeStops)
+          .set({ stopOrder: -(i + 1), updatedAt: now })
+          .where(eq(routeStops.id, newOrderIds[i]!));
+      }
+      for (let i = 0; i < newOrderIds.length; i++) {
+        const leg = legs[i]!;
+        await tx
+          .update(routeStops)
+          .set({
+            stopOrder: i + 1,
+            travelMinsFromPrev: leg.travelMinsFromPrev,
+            travelDistanceKmFromPrev:
+              leg.travelDistanceKmFromPrev == null
+                ? null
+                : leg.travelDistanceKmFromPrev.toFixed(2),
+            bufferMins: i === 0 ? 0 : bufferMins,
+            updatedAt: now,
+          })
+          .where(eq(routeStops.id, newOrderIds[i]!));
+      }
+      await tx
+        .update(groomerRoutes)
+        .set({
+          totalTravelMins,
+          totalDistanceKm: totalDistanceKm.toFixed(2),
+          updatedAt: now,
+        })
+        .where(eq(groomerRoutes.id, routeId));
+    });
+
+    const [updatedRoute] = await db
+      .select()
+      .from(groomerRoutes)
+      .where(eq(groomerRoutes.id, routeId));
+    const stops = await loadRouteStops(db, routeId);
+    const annotated = annotateConflicts(stops);
+    return c.json({
+      route: updatedRoute,
+      stops: annotated.stops,
+      hasConflicts: annotated.hasConflicts,
+      conflictCount: annotated.conflictCount,
+    });
+  }
+);
+
+/**
+ * GET /:routeId/export/:platform — build a native-navigation deep-link URL for an
+ * optimized route. Origin = first stop, destination = last stop, the rest carried
+ * as ordered intermediate waypoints. Waypoint count is validated against the
+ * platform's limit. Auth: manager (any route) or groomer (own route only).
+ */
+async function handleNavigationExport(
+  c: Context<AppEnv>,
+  platform: NavigationPlatform
+) {
+  const db = getDb();
+  const routeId = c.req.param("routeId");
+  if (!routeId || !z.string().uuid().safeParse(routeId).success) {
+    return c.json({ error: "routeId must be a UUID" }, 400);
+  }
+
+  const [route] = await db
+    .select()
+    .from(groomerRoutes)
+    .where(eq(groomerRoutes.id, routeId));
+  if (!route) {
+    return c.json({ error: "Route not found" }, 404);
+  }
+
+  // Reuse the groomer-own / manager authorization rule against the route owner.
+  const resolved = resolveTargetStaffId(c.get("staff"), route.staffId);
+  if ("error" in resolved) {
+    return c.json({ error: resolved.error }, resolved.status);
+  }
+
+  const stops = await loadRouteStops(db, routeId);
+  if (stops.length === 0) {
+    return c.json({ error: "route has no stops to export" }, 400);
+  }
+
+  const navStops: NavigationStop[] = stops.map((s) => ({
+    latitude: s.latitude,
+    longitude: s.longitude,
+    label: s.clientName,
+  }));
+
+  const result = buildNavigationUrl(platform, navStops);
+  if ("error" in result) {
+    return c.json({ error: result.error }, result.status);
+  }
+
+  return c.json({
+    platform: result.platform,
+    url: result.url,
+    stopCount: result.stopCount,
+    waypointCount: result.waypointCount,
+  });
+}
+
+routesRouter.get("/:routeId/export/google-maps", (c) =>
+  handleNavigationExport(c, "google-maps")
+);
+
+routesRouter.get("/:routeId/export/apple-maps", (c) =>
+  handleNavigationExport(c, "apple-maps")
+);

src/routes/settings.ts

@@ -7,6 +7,17 @@ import { requireSuperUser } from "../middleware/rbac.js";
 
 export const settingsRouter = new Hono();
 
+type BusinessSettingsRow = typeof businessSettings.$inferSelect;
+
+// Strip the encrypted googleMapsApiKey ciphertext from settings responses
+// (GRO-2294, defense-in-depth). The secret is never needed client-side; it is
+// only written via the dedicated provider-config endpoint.
+function redactSettings(row: BusinessSettingsRow) {
+  const rest: Partial<BusinessSettingsRow> = { ...row };
+  delete rest.googleMapsApiKey;
+  return rest;
+}
+
 // GET /api/admin/settings — return current business settings
 settingsRouter.get("/", async (c) => {
   const db = getDb();
@@ -14,9 +25,10 @@ settingsRouter.get("/", async (c) => {
   if (!row) {
     // Auto-create default settings if none exist
     const [created] = await db.insert(businessSettings).values({}).returning();
-    return c.json(created);
+    if (!created) throw new Error("Failed to create default settings");
+    return c.json(redactSettings(created));
   }
-  return c.json(row);
+  return c.json(redactSettings(row));
 });
 
 const hexColorRegex = /^#[0-9a-fA-F]{6}$/;

src/services/navigationExport.ts

@@ -0,0 +1,155 @@
+// Navigation export — turn an optimized groomer route into a deep-link URL that
+// opens the device's native navigation app (Google Maps / Apple Maps).
+//
+// A route is exported as: origin = first stop, destination = last stop, with the
+// in-between stops carried as ordered intermediate waypoints. Each platform caps
+// how many intermediate waypoints a deep link may carry, so callers must validate
+// the route length before handing the URL to the client.
+
+/**
+ * Max intermediate waypoints a Google Maps URLs API deep link supports
+ * (`https://www.google.com/maps/dir/?api=1&...&waypoints=...`). Google documents
+ * a ceiling of 9 waypoints between origin and destination.
+ */
+export const GOOGLE_MAPS_MAX_WAYPOINTS = 9;
+
+/**
+ * Max intermediate waypoints we allow in an Apple Maps `maps://` deep link. Apple's
+ * URL scheme chains destinations with `+to:` but does not publish a hard cap; 15 is
+ * a conservative practical limit that keeps the URL well under length limits.
+ */
+export const APPLE_MAPS_MAX_WAYPOINTS = 15;
+
+export type NavigationPlatform = "google-maps" | "apple-maps";
+
+/** A single ordered point on the route. `label` is optional, for display only. */
+export interface NavigationStop {
+  latitude: number;
+  longitude: number;
+  label?: string | null;
+}
+
+export interface NavigationExportSuccess {
+  platform: NavigationPlatform;
+  url: string;
+  /** Total stops included (origin + waypoints + destination). */
+  stopCount: number;
+  /** Intermediate waypoints only (excludes origin and destination). */
+  waypointCount: number;
+}
+
+export interface NavigationExportError {
+  error: string;
+  status: 400;
+}
+
+export type NavigationExportResult =
+  | NavigationExportSuccess
+  | NavigationExportError;
+
+function isError(r: NavigationExportResult): r is NavigationExportError {
+  return "error" in r;
+}
+
+/** Intermediate waypoints = every stop that is neither origin nor destination. */
+export function intermediateWaypointCount(stopCount: number): number {
+  return Math.max(0, stopCount - 2);
+}
+
+function coord(stop: NavigationStop): string {
+  return `${stop.latitude},${stop.longitude}`;
+}
+
+/**
+ * Builds a Google Maps URLs API driving deep link. On mobile this opens the
+ * native Google Maps app; on desktop it opens maps.google.com.
+ */
+export function buildGoogleMapsUrl(
+  stops: NavigationStop[]
+): NavigationExportResult {
+  if (stops.length === 0) {
+    return { error: "route has no stops to export", status: 400 };
+  }
+  const waypointCount = intermediateWaypointCount(stops.length);
+  if (waypointCount > GOOGLE_MAPS_MAX_WAYPOINTS) {
+    return {
+      error: `route has ${waypointCount} intermediate waypoints, exceeding Google Maps' limit of ${GOOGLE_MAPS_MAX_WAYPOINTS}`,
+      status: 400,
+    };
+  }
+
+  const origin = stops[0]!;
+  const destination = stops[stops.length - 1]!;
+  const params = new URLSearchParams();
+  params.set("api", "1");
+  params.set("travelmode", "driving");
+  params.set("origin", coord(origin));
+  params.set("destination", coord(destination));
+  if (stops.length > 2) {
+    const mids = stops
+      .slice(1, -1)
+      .map(coord)
+      .join("|");
+    params.set("waypoints", mids);
+  }
+
+  return {
+    platform: "google-maps",
+    url: `https://www.google.com/maps/dir/?${params.toString()}`,
+    stopCount: stops.length,
+    waypointCount,
+  };
+}
+
+/**
+ * Builds an Apple Maps `maps://` driving deep link. The first stop is the source
+ * (`saddr`); the remaining stops are chained as destinations with `+to:` (`daddr`).
+ * Built by hand because the `+to:` separators are part of Apple's scheme and must
+ * not be percent-encoded.
+ */
+export function buildAppleMapsUrl(
+  stops: NavigationStop[]
+): NavigationExportResult {
+  if (stops.length === 0) {
+    return { error: "route has no stops to export", status: 400 };
+  }
+  const waypointCount = intermediateWaypointCount(stops.length);
+  if (waypointCount > APPLE_MAPS_MAX_WAYPOINTS) {
+    return {
+      error: `route has ${waypointCount} intermediate waypoints, exceeding Apple Maps' limit of ${APPLE_MAPS_MAX_WAYPOINTS}`,
+      status: 400,
+    };
+  }
+
+  const params: string[] = ["dirflg=d"];
+  if (stops.length === 1) {
+    // Single stop: destination only, no source.
+    params.unshift(`daddr=${coord(stops[0]!)}`);
+  } else {
+    const daddr = stops
+      .slice(1)
+      .map(coord)
+      .join("+to:");
+    params.unshift(`daddr=${daddr}`);
+    params.unshift(`saddr=${coord(stops[0]!)}`);
+  }
+
+  return {
+    platform: "apple-maps",
+    url: `maps://?${params.join("&")}`,
+    stopCount: stops.length,
+    waypointCount,
+  };
+}
+
+/** Dispatches to the correct builder for the requested platform. */
+export function buildNavigationUrl(
+  platform: NavigationPlatform,
+  stops: NavigationStop[]
+): NavigationExportResult {
+  return platform === "google-maps"
+    ? buildGoogleMapsUrl(stops)
+    : buildAppleMapsUrl(stops);
+}
+
+export { isError as isNavigationExportError };

src/services/routeOptimization.ts

@@ -0,0 +1,513 @@
+import { businessSettings, decryptSecret, type Db } from "@groombook/db";
+import type { FetchLike } from "./geocoding.js";
+
+/**
+ * Route optimization service (GRO-2155, Phase 2.1 of Route Optimization).
+ *
+ * Given a groomer's geocoded stops for a day, produces an optimized visiting
+ * order plus per-leg and total travel estimates. Two strategies:
+ *
+ * - {@link optimizeWithGoogle}: Google Maps Directions API with
+ *   `optimizeWaypoints: true` (real road durations/distances), used when a
+ *   Google Maps API key is configured.
+ * - {@link nearestNeighborOrder}: an offline nearest-neighbor TSP heuristic over
+ *   great-circle distance, used as the default free / no-API-key fallback.
+ *
+ * Both strategies share the same public {@link optimizeRoute} orchestrator,
+ * which also handles the >25-stop edge case by chunking into sub-routes (the
+ * Google Directions waypoint cap) and surfacing a warning.
+ */
+
+/** Google Directions allows origin + destination + up to 23 waypoints = 25
+ * points per request. We cap a sub-route at 25 stops and chunk beyond that. */
+export const MAX_STOPS_PER_ROUTE = 25;
+
+/** Average driving speed (km/h) used to convert distance into travel minutes in
+ * the offline heuristic. Tuned for mixed urban/suburban mobile-groomer routes. */
+export const AVG_SPEED_KMH = 40;
+
+/** Multiplier applied to great-circle distance to approximate real road
+ * distance in the offline heuristic (straight-line underestimates driving). */
+export const ROAD_CIRCUITY_FACTOR = 1.3;
+
+const EARTH_RADIUS_KM = 6371;
+
+/** A geocoded stop to be ordered. `appointmentId` ties it back to the schedule. */
+export interface RouteStopInput {
+  appointmentId: string;
+  latitude: number;
+  longitude: number;
+}
+
+/** A single stop in the optimized order, with travel from the previous stop. */
+export interface OptimizedStop {
+  appointmentId: string;
+  latitude: number;
+  longitude: number;
+  /** Null for the first stop of the whole route. */
+  travelMinsFromPrev: number | null;
+  /** Null for the first stop of the whole route. Kilometres, 2-dp. */
+  travelDistanceKmFromPrev: number | null;
+}
+
+export type RouteOptimizationProvider = "google" | "nearest_neighbor";
+
+export interface OptimizedRoute {
+  provider: RouteOptimizationProvider;
+  stops: OptimizedStop[];
+  totalTravelMins: number;
+  /** Kilometres, rounded to 2 decimal places. */
+  totalDistanceKm: number;
+  /** True when the route was split into multiple sub-routes (>25 stops). */
+  chunked: boolean;
+  subRouteCount: number;
+  /** Non-fatal advisories for the caller to surface to the user. */
+  warnings: string[];
+}
+
+export interface OptimizeRouteOptions {
+  /** Google Maps API key. When absent, the nearest-neighbor heuristic is used. */
+  googleApiKey?: string | null;
+  /** Injectable fetch for testing the Google path. Defaults to global fetch. */
+  fetchImpl?: FetchLike;
+}
+
+const defaultFetch: FetchLike = (input, init) =>
+  (globalThis.fetch as unknown as FetchLike)(input, init);
+
+// ─── Geometry helpers ───────────────────────────────────────────────────────
+
+function toRadians(deg: number): number {
+  return (deg * Math.PI) / 180;
+}
+
+/** Great-circle distance between two coordinates, in kilometres. */
+export function haversineKm(
+  a: { latitude: number; longitude: number },
+  b: { latitude: number; longitude: number }
+): number {
+  const dLat = toRadians(b.latitude - a.latitude);
+  const dLon = toRadians(b.longitude - a.longitude);
+  const lat1 = toRadians(a.latitude);
+  const lat2 = toRadians(b.latitude);
+  const h =
+    Math.sin(dLat / 2) ** 2 +
+    Math.cos(lat1) * Math.cos(lat2) * Math.sin(dLon / 2) ** 2;
+  return 2 * EARTH_RADIUS_KM * Math.asin(Math.min(1, Math.sqrt(h)));
+}
+
+/** Round to 2 decimal places, returning a finite number. */
+function round2(n: number): number {
+  return Math.round(n * 100) / 100;
+}
+
+/**
+ * Estimate a road travel leg from the great-circle distance between two points.
+ * Applies a circuity factor for distance and a fixed average speed for time.
+ */
+export function estimateLeg(
+  a: { latitude: number; longitude: number },
+  b: { latitude: number; longitude: number }
+): { distanceKm: number; mins: number } {
+  const straight = haversineKm(a, b);
+  const distanceKm = straight * ROAD_CIRCUITY_FACTOR;
+  const mins = (distanceKm / AVG_SPEED_KMH) * 60;
+  return { distanceKm: round2(distanceKm), mins: Math.round(mins) };
+}
+
+// ─── Nearest-neighbor heuristic ─────────────────────────────────────────────
+
+/**
+ * Orders points greedily: start at `startIndex`, then repeatedly visit the
+ * nearest unvisited point (great-circle distance). Returns indices into the
+ * input array in visiting order. Deterministic ties broken by lowest index.
+ */
+export function nearestNeighborOrder(
+  points: Array<{ latitude: number; longitude: number }>,
+  startIndex = 0
+): number[] {
+  const n = points.length;
+  if (n <= 1) return points.map((_, i) => i);
+
+  const visited = new Array<boolean>(n).fill(false);
+  const order: number[] = [startIndex];
+  visited[startIndex] = true;
+  let current = startIndex;
+
+  for (let step = 1; step < n; step++) {
+    let best = -1;
+    let bestDist = Infinity;
+    for (let j = 0; j < n; j++) {
+      if (visited[j]) continue;
+      const d = haversineKm(points[current]!, points[j]!);
+      if (d < bestDist) {
+        bestDist = d;
+        best = j;
+      }
+    }
+    visited[best] = true;
+    order.push(best);
+    current = best;
+  }
+  return order;
+}
+
+/** Orders one chunk (<= MAX_STOPS_PER_ROUTE) via nearest-neighbor. */
+function optimizeChunkNearestNeighbor(
+  stops: RouteStopInput[]
+): RouteStopInput[] {
+  const order = nearestNeighborOrder(stops, 0);
+  return order.map((i) => stops[i]!);
+}
+
+// ─── Google Directions ──────────────────────────────────────────────────────
+
+const GOOGLE_DIRECTIONS_URL =
+  "https://maps.googleapis.com/maps/api/directions/json";
+
+interface GoogleDirectionsResponse {
+  status: string;
+  error_message?: string;
+  routes?: Array<{
+    waypoint_order?: number[];
+    legs?: Array<{
+      duration?: { value?: number };
+      distance?: { value?: number };
+    }>;
+  }>;
+}
+
+/**
+ * Orders one chunk via the Google Directions API with `optimizeWaypoints=true`.
+ *
+ * The first stop is fixed as both origin and destination (a closed tour); the
+ * remaining stops are passed as optimizable waypoints. We keep the optimized
+ * forward order and drop the final return-to-origin leg, yielding an open route
+ * whose per-leg durations/distances come from real road data.
+ */
+async function optimizeChunkGoogle(
+  stops: RouteStopInput[],
+  apiKey: string,
+  fetchImpl: FetchLike
+): Promise<{ stops: RouteStopInput[]; legsMeters: number[]; legsSeconds: number[] }> {
+  if (stops.length <= 1) {
+    return { stops: [...stops], legsMeters: [], legsSeconds: [] };
+  }
+
+  const origin = stops[0]!;
+  const waypoints = stops.slice(1);
+  const url = new URL(GOOGLE_DIRECTIONS_URL);
+  url.searchParams.set("origin", `${origin.latitude},${origin.longitude}`);
+  url.searchParams.set("destination", `${origin.latitude},${origin.longitude}`);
+  url.searchParams.set(
+    "waypoints",
+    "optimize:true|" +
+      waypoints.map((w) => `${w.latitude},${w.longitude}`).join("|")
+  );
+  url.searchParams.set("key", apiKey);
+
+  const res = await fetchImpl(url.toString());
+  if (!res.ok) {
+    throw new Error(
+      `Google Directions request failed: ${res.status} ${res.statusText}`
+    );
+  }
+  const body = (await res.json()) as GoogleDirectionsResponse;
+  if (body.status !== "OK" || !body.routes || body.routes.length === 0) {
+    throw new Error(
+      `Google Directions returned status ${body.status}${
+        body.error_message ? `: ${body.error_message}` : ""
+      }`
+    );
+  }
+
+  const route = body.routes[0]!;
+  const waypointOrder = route.waypoint_order ?? waypoints.map((_, i) => i);
+  const legs = route.legs ?? [];
+
+  // Ordered stops: origin first, then waypoints in the optimized order.
+  const orderedStops: RouteStopInput[] = [
+    origin,
+    ...waypointOrder.map((i) => waypoints[i]!),
+  ];
+
+  // legs[k] is the travel into orderedStops[k+1]. Drop the trailing return leg
+  // (orderedStops.length-1 legs describe the open route).
+  const legsMeters: number[] = [];
+  const legsSeconds: number[] = [];
+  for (let k = 0; k < orderedStops.length - 1; k++) {
+    const leg = legs[k];
+    legsMeters.push(leg?.distance?.value ?? 0);
+    legsSeconds.push(leg?.duration?.value ?? 0);
+  }
+
+  return { stops: orderedStops, legsMeters, legsSeconds };
+}
+
+// ─── Orchestration ──────────────────────────────────────────────────────────
+
+function chunk<T>(items: T[], size: number): T[][] {
+  const out: T[][] = [];
+  for (let i = 0; i < items.length; i += size) {
+    out.push(items.slice(i, i + size));
+  }
+  return out;
+}
+
+/**
+ * Optimizes a full day's stops into a single visiting order with travel
+ * metrics. Uses Google Directions when `googleApiKey` is provided, otherwise the
+ * offline nearest-neighbor heuristic. Routes longer than
+ * {@link MAX_STOPS_PER_ROUTE} stops are split into sub-routes and a warning is
+ * emitted; sub-routes are stitched end-to-end, with the boundary leg estimated
+ * from great-circle distance.
+ */
+export async function optimizeRoute(
+  inputStops: RouteStopInput[],
+  options: OptimizeRouteOptions = {}
+): Promise<OptimizedRoute> {
+  const fetchImpl = options.fetchImpl ?? defaultFetch;
+  const useGoogle = Boolean(options.googleApiKey);
+  const provider: RouteOptimizationProvider = useGoogle
+    ? "google"
+    : "nearest_neighbor";
+  const warnings: string[] = [];
+
+  if (inputStops.length === 0) {
+    return {
+      provider,
+      stops: [],
+      totalTravelMins: 0,
+      totalDistanceKm: 0,
+      chunked: false,
+      subRouteCount: 0,
+      warnings,
+    };
+  }
+
+  const chunks = chunk(inputStops, MAX_STOPS_PER_ROUTE);
+  const chunked = chunks.length > 1;
+  if (chunked) {
+    warnings.push(
+      `Route has ${inputStops.length} stops, exceeding the ${MAX_STOPS_PER_ROUTE}-stop optimization limit. Split into ${chunks.length} sub-routes; review the order at sub-route boundaries.`
+    );
+  }
+
+  const ordered: OptimizedStop[] = [];
+  let prev: RouteStopInput | null = null;
+
+  for (const group of chunks) {
+    let groupStops: RouteStopInput[];
+    let legDistanceKm: (i: number) => number;
+    let legMins: (i: number) => number;
+
+    if (useGoogle) {
+      try {
+        const result = await optimizeChunkGoogle(
+          group,
+          options.googleApiKey!,
+          fetchImpl
+        );
+        groupStops = result.stops;
+        legDistanceKm = (i) => round2(result.legsMeters[i]! / 1000);
+        legMins = (i) => Math.round(result.legsSeconds[i]! / 60);
+      } catch (err) {
+        // Google failed mid-optimization — degrade to the offline heuristic for
+        // this run rather than failing the whole request.
+        warnings.push(
+          `Google Directions unavailable; used offline heuristic: ${
+            err instanceof Error ? err.message : String(err)
+          }`
+        );
+        groupStops = optimizeChunkNearestNeighbor(group);
+        legDistanceKm = (i) => estimateLeg(groupStops[i]!, groupStops[i + 1]!).distanceKm;
+        legMins = (i) => estimateLeg(groupStops[i]!, groupStops[i + 1]!).mins;
+      }
+    } else {
+      groupStops = optimizeChunkNearestNeighbor(group);
+      legDistanceKm = (i) => estimateLeg(groupStops[i]!, groupStops[i + 1]!).distanceKm;
+      legMins = (i) => estimateLeg(groupStops[i]!, groupStops[i + 1]!).mins;
+    }
+
+    for (let i = 0; i < groupStops.length; i++) {
+      const stop = groupStops[i]!;
+      if (prev === null) {
+        // Very first stop of the whole route.
+        ordered.push({
+          appointmentId: stop.appointmentId,
+          latitude: stop.latitude,
+          longitude: stop.longitude,
+          travelMinsFromPrev: null,
+          travelDistanceKmFromPrev: null,
+        });
+      } else if (i === 0) {
+        // First stop of a non-initial chunk: estimate the boundary leg.
+        const est = estimateLeg(prev, stop);
+        ordered.push({
+          appointmentId: stop.appointmentId,
+          latitude: stop.latitude,
+          longitude: stop.longitude,
+          travelMinsFromPrev: est.mins,
+          travelDistanceKmFromPrev: est.distanceKm,
+        });
+      } else {
+        ordered.push({
+          appointmentId: stop.appointmentId,
+          latitude: stop.latitude,
+          longitude: stop.longitude,
+          travelMinsFromPrev: legMins(i - 1),
+          travelDistanceKmFromPrev: legDistanceKm(i - 1),
+        });
+      }
+      prev = stop;
+    }
+  }
+
+  const totalTravelMins = ordered.reduce(
+    (sum, s) => sum + (s.travelMinsFromPrev ?? 0),
+    0
+  );
+  const totalDistanceKm = round2(
+    ordered.reduce((sum, s) => sum + (s.travelDistanceKmFromPrev ?? 0), 0)
+  );
+
+  return {
+    provider,
+    stops: ordered,
+    totalTravelMins,
+    totalDistanceKm,
+    chunked,
+    subRouteCount: chunks.length,
+    warnings,
+  };
+}
+
+// ─── Google API key resolution ──────────────────────────────────────────────
+
+/**
+ * Resolves the Google Maps API key for route optimization from
+ * `businessSettings.googleMapsApiKey` (decrypted at rest) or, as a development
+ * convenience, the `GOOGLE_MAPS_API_KEY` env var. Returns `null` when no usable
+ * key exists, in which case callers fall back to the offline heuristic.
+ */
+export async function resolveRouteGoogleApiKey(
+  db: Db,
+  decrypt: (ciphertext: string) => string = decryptSecret
+): Promise<string | null> {
+  const [settings] = await db.select().from(businessSettings).limit(1);
+  const stored = settings?.googleMapsApiKey?.trim();
+  if (stored) {
+    try {
+      const decrypted = decrypt(stored).trim();
+      if (decrypted) return decrypted;
+    } catch (err) {
+      console.warn(
+        `Failed to decrypt googleMapsApiKey for route optimization; using offline heuristic: ${
+          err instanceof Error ? err.message : String(err)
+        }`
+      );
+    }
+  }
+  const fromEnv = process.env.GOOGLE_MAPS_API_KEY?.trim();
+  return fromEnv ? fromEnv : null;
+}
+
+// ─── Travel buffer & schedule-conflict logic (GRO-2156, Phase 2.2) ───────────
+
+/** A single stop's timing inputs for schedule-conflict detection. */
+export interface ScheduleStopTiming {
+  /** Scheduled appointment start. */
+  appointmentStartTime: Date;
+  /** Scheduled appointment end. */
+  appointmentEndTime: Date;
+  /** Travel minutes into this stop from the previous one (null for first). */
+  travelMinsFromPrev: number | null;
+  /** Configured buffer minutes before this stop. */
+  bufferMins: number;
+}
+
+/** Conflict annotation for one stop, surfaced for the frontend to display. */
+export interface StopConflictFlags {
+  /** True when the schedule gap is too tight for travel + buffer. */
+  hasConflict: boolean;
+  /** Minutes between the previous appointment's end and this one's start.
+   * Null for the first stop (no predecessor). */
+  scheduleGapMins: number | null;
+  /** travelMinsFromPrev + bufferMins. Null for the first stop. */
+  requiredGapMins: number | null;
+  /** requiredGapMins − scheduleGapMins; positive when the schedule is tight.
+   * Null for the first stop. */
+  shortfallMins: number | null;
+}
+
+const MS_PER_MIN = 60_000;
+
+/**
+ * Detects "tight schedule" conflicts between consecutive stops, in visiting
+ * order. A conflict exists when the real gap between the previous appointment's
+ * end and this appointment's start is smaller than the time needed to travel
+ * plus the configured buffer (`travelMinsFromPrev + bufferMins`).
+ *
+ * This only *flags* conflicts — appointments are never moved. The first stop
+ * has no predecessor and is therefore always conflict-free.
+ */
+export function detectScheduleConflicts(
+  stops: ScheduleStopTiming[]
+): StopConflictFlags[] {
+  return stops.map((s, i) => {
+    if (i === 0) {
+      return {
+        hasConflict: false,
+        scheduleGapMins: null,
+        requiredGapMins: null,
+        shortfallMins: null,
+      };
+    }
+    const prev = stops[i - 1]!;
+    const scheduleGapMins = Math.round(
+      (s.appointmentStartTime.getTime() - prev.appointmentEndTime.getTime()) /
+        MS_PER_MIN
+    );
+    const requiredGapMins = (s.travelMinsFromPrev ?? 0) + s.bufferMins;
+    const shortfallMins = requiredGapMins - scheduleGapMins;
+    return {
+      hasConflict: shortfallMins > 0,
+      scheduleGapMins,
+      requiredGapMins,
+      shortfallMins,
+    };
+  });
+}
+
+/** A coordinate used when recomputing legs for a fixed (manually chosen) order. */
+export interface OrderedPoint {
+  latitude: number;
+  longitude: number;
+}
+
+/** Recomputed per-leg travel for a fixed stop order. */
+export interface RecomputedLeg {
+  /** Null for the first stop. */
+  travelMinsFromPrev: number | null;
+  /** Null for the first stop. Kilometres, 2-dp. */
+  travelDistanceKmFromPrev: number | null;
+}
+
+/**
+ * Recomputes per-leg travel estimates for a *fixed* visiting order (e.g. after a
+ * manual reorder). Unlike {@link optimizeRoute} this does not reorder anything —
+ * it walks the given order and estimates each leg offline via {@link estimateLeg}
+ * so a manual drag does not consume Google Directions quota.
+ */
+export function recomputeLegsForOrder(points: OrderedPoint[]): RecomputedLeg[] {
+  return points.map((p, i) => {
+    if (i === 0) {
+      return { travelMinsFromPrev: null, travelDistanceKmFromPrev: null };
+    }
+    const est = estimateLeg(points[i - 1]!, p);
+    return {
+      travelMinsFromPrev: est.mins,
+      travelDistanceKmFromPrev: est.distanceKm,
+    };
+  });
+}