fix(portal): validate waitlist preferredTime/preferredDate, return 400 on bad input (GRO-2211)

createWaitlistEntrySchema/updateWaitlistEntrySchema declared preferredTime/
preferredDate as bare z.string(), so a malformed value (e.g. a full ISO
datetime) was inserted straight into the Postgres time/date columns, throwing
a DateTimeParseError that surfaced as an unhandled 500.

Constrain both fields with regexes (HH:MM[:SS] / YYYY-MM-DD) so zValidator
rejects bad input with 400 before it hits the DB, and normalize HH:MM to
HH:MM:SS on insert/update. Adds waitlist tests covering the 400 paths and
HH:MM normalization.

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

UAT_PLAYBOOK.md

@@ -281,6 +281,7 @@ 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 |
 
 ### 4.9 Waitlist
 
@@ -358,6 +359,24 @@ 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: at least one geocoded client with appointments on the target date for the staff member (use §4.2 geocoding + a seed groomer).
+
+| # | 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). Each stop carries `bufferMins` (default 15) |
+| 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`) |
+
 ## Pass/Fail Criteria
 
 **Pass:**

packages/db/package.json

@@ -18,9 +18,10 @@
   "scripts": {
     "build": "tsc --project .",
     "generate": "drizzle-kit generate",
-    "migrate": "drizzle-kit migrate",
-    "seed": "tsx src/seed.ts",
-    "reset": "tsx src/reset.ts && drizzle-kit migrate && tsx src/seed.ts",
+    "wait-for-db": "node ./scripts/wait-for-db.mjs",
+    "migrate": "node ./scripts/wait-for-db.mjs && drizzle-kit migrate",
+    "seed": "node ./scripts/wait-for-db.mjs && tsx src/seed.ts",
+    "reset": "node ./scripts/wait-for-db.mjs && tsx src/reset.ts && drizzle-kit migrate && tsx src/seed.ts",
     "studio": "drizzle-kit studio",
     "typecheck": "tsc --noEmit"
   },

packages/db/scripts/wait-for-db.mjs

@@ -0,0 +1,104 @@
+#!/usr/bin/env node
+// wait-for-db.mjs
+//
+// GRO-2163: wait for / retry DNS resolution of the database hostname derived
+// from DATABASE_URL before invoking `drizzle-kit migrate`. The first attempt
+// of a fresh migrate-schema pod occasionally hits a transient CoreDNS miss
+// (EAI_AGAIN) on `groombook-postgres-rw.<ns>.svc`; with backoffLimit: 2 the
+// retry pod usually wins, but three unlucky attempts in a row trips
+// BackoffLimitExceeded. Resolving once here, with backoff, removes the dice
+// roll at the source so the first attempt reliably succeeds.
+//
+// Mirrors the belt-and-braces pattern used in GRO-1985 (no Corepack
+// download fallback): we don't try to outsmart CoreDNS, we just don't ask
+// drizzle-kit to do the very first DNS lookup of a freshly-scheduled pod.
+//
+// Configuration (env):
+//   WAIT_FOR_DB_MAX_ATTEMPTS  default 12  (~30s of total wait at default backoff)
+//   WAIT_FOR_DB_BASE_DELAY_MS default 500
+//   WAIT_FOR_DB_MAX_DELAY_MS  default 5000
+//   WAIT_FOR_DB_SKIP          default unset; set to "1" to skip (debug only)
+//
+// On success: exit 0. On exhaustion: exit 1 so the Job's backoff is
+// preserved (we don't want to silently mask a real outage by giving up
+// after 30s and letting drizzle-kit fail with a less-actionable error).
+
+import { setTimeout as delay } from "node:timers/promises";
+import dns from "node:dns/promises";
+
+const MAX_ATTEMPTS = Number(process.env.WAIT_FOR_DB_MAX_ATTEMPTS ?? 12);
+const BASE_DELAY_MS = Number(process.env.WAIT_FOR_DB_BASE_DELAY_MS ?? 500);
+const MAX_DELAY_MS = Number(process.env.WAIT_FOR_DB_MAX_DELAY_MS ?? 5000);
+
+function parseHost(databaseUrl) {
+  try {
+    return new URL(databaseUrl).hostname || null;
+  } catch {
+    return null;
+  }
+}
+
+async function resolveOnce(host) {
+  const start = Date.now();
+  const result = await dns.lookup(host);
+  return { address: result.address, ms: Date.now() - start };
+}
+
+async function main() {
+  if (process.env.WAIT_FOR_DB_SKIP === "1") {
+    console.log("[wait-for-db] WAIT_FOR_DB_SKIP=1, skipping");
+    return;
+  }
+  const databaseUrl = process.env.DATABASE_URL;
+  if (!databaseUrl) {
+    // Don't gate the migrate on a misconfigured env — let drizzle-kit fail
+    // loudly with its own clear error.
+    console.warn("[wait-for-db] DATABASE_URL not set; skipping");
+    return;
+  }
+  const host = parseHost(databaseUrl);
+  if (!host) {
+    console.warn(`[wait-for-db] could not parse hostname from DATABASE_URL; skipping`);
+    return;
+  }
+  console.log(
+    `[wait-for-db] host=${host} max_attempts=${MAX_ATTEMPTS} ` +
+      `base_delay_ms=${BASE_DELAY_MS} max_delay_ms=${MAX_DELAY_MS}`,
+  );
+
+  for (let attempt = 1; attempt <= MAX_ATTEMPTS; attempt++) {
+    try {
+      const { address, ms } = await resolveOnce(host);
+      console.log(`[wait-for-db] ok attempt=${attempt} host=${host} -> ${address} (${ms}ms)`);
+      return;
+    } catch (err) {
+      const code = err?.code ?? "UNKNOWN";
+      const transient = code === "EAI_AGAIN" || code === "ENOTFOUND" || code === "EAI_NODATA";
+      if (!transient) {
+        // Hard error (e.g. invalid hostname): surface and let drizzle-kit fail
+        // with a real error rather than spinning.
+        console.error(`[wait-for-db] non-transient DNS error attempt=${attempt} code=${code}: ${err.message}`);
+        process.exit(1);
+      }
+      if (attempt === MAX_ATTEMPTS) {
+        console.error(
+          `[wait-for-db] exhausted attempts=${MAX_ATTEMPTS} host=${host} last_code=${code}; exiting 1`,
+        );
+        process.exit(1);
+      }
+      const backoff = Math.min(
+        MAX_DELAY_MS,
+        BASE_DELAY_MS * 2 ** (attempt - 1) + Math.floor(Math.random() * BASE_DELAY_MS),
+      );
+      console.log(
+        `[wait-for-db] transient attempt=${attempt} code=${code} retry_in_ms=${backoff}`,
+      );
+      await delay(backoff);
+    }
+  }
+}
+
+main().catch((err) => {
+  console.error(`[wait-for-db] fatal: ${err?.message ?? err}`);
+  process.exit(1);
+});

src/__tests__/portalPets.test.ts

@@ -177,7 +177,10 @@ describe("PATCH /portal/pets/:petId", () => {
     expect(persisted.weightKg).toBe("18.25");
     expect(persisted.groomingNotes).toBe("old grooming notes");
     expect(persisted.healthAlerts).toBe("Allergic to oatmeal shampoo");
-    expect(persisted.photoKey).toBe("pets/rex.jpg");
+    // photoKey is NOT writable via portal PATCH (GRO-2187 S3 key-hijack fix):
+    // the web form round-trips the GET-shaped photoUrl, but the server must not
+    // persist it. Photo changes go through the key-validated upload flow.
+    expect(persisted.photoKey).toBeUndefined();
     expect(persisted.coatType).toBe("double");
     expect(persisted.petSizeCategory).toBe("extra_large");
     expect(persisted.preferredCuts).toEqual(["teddy bear", "puppy cut"]);
@@ -187,6 +190,55 @@ describe("PATCH /portal/pets/:petId", () => {
     expect(persisted.updatedAt).toBeInstanceOf(Date);
   });
 
+  // GRO-2187 security regression: a portal customer must not be able to set the
+  // S3 object key. photoKey is consumed server-side by getPresignedGetUrl /
+  // deleteObject; the upload path guards keys with a pets/{petId}/ prefix, and the
+  // portal PATCH must not offer a bypass. A foreign/arbitrary photoUrl is accepted
+  // (Zod strips the unknown key) but must leave photoKey untouched.
+  it("does not mutate photoKey when a foreign photoUrl is supplied (200)", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    const ownKey = `pets/${PET_ID}/original.jpg`;
+    selectPetRow = { ...PET, photoKey: ownKey };
+
+    const res = await jsonPatch(
+      `/portal/pets/${PET_ID}`,
+      {
+        name: "Rex",
+        // attacker-chosen key pointing at another tenant's object
+        photoUrl: "pets/00000000-0000-0000-0000-0000000000ff/victim-secret.jpg",
+      },
+      { "X-Impersonation-Session-Id": SESSION_ID }
+    );
+
+    expect(res.status).toBe(200);
+    const persisted = updatedValues[0]!;
+    // The attacker-supplied key never reaches the update payload.
+    expect(persisted.photoKey).toBeUndefined();
+    // And the stored key is unchanged from the pet's own value.
+    const body = await res.json();
+    expect(body.photoUrl).toBe(ownKey);
+  });
+
+  // The length/array caps live in the Zod schema, so violations are rejected by
+  // zValidator with 400 (in-handler enum checks are what return 422).
+  it("returns 400 when a medicalAlert description exceeds the length cap", async () => {
+    selectSessionRow = ACTIVE_SESSION;
+    selectPetRow = PET;
+
+    const res = await jsonPatch(
+      `/portal/pets/${PET_ID}`,
+      {
+        medicalAlerts: [
+          { type: "allergy", description: "x".repeat(2001), severity: "low" },
+        ],
+      },
+      { "X-Impersonation-Session-Id": SESSION_ID }
+    );
+
+    expect(res.status).toBe(400);
+    expect(updatedValues).toHaveLength(0);
+  });
+
   it("falls back to the weight key when weightKg is absent", async () => {
     selectSessionRow = ACTIVE_SESSION;
     selectPetRow = PET;
@@ -228,6 +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__/routeOptimization.test.ts

@@ -0,0 +1,184 @@
+import { describe, it, expect } from "vitest";
+import {
+  haversineKm,
+  estimateLeg,
+  nearestNeighborOrder,
+  optimizeRoute,
+  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);
+  });
+});

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/routes/portal.ts

@@ -261,8 +261,8 @@ const PORTAL_PET_SIZE_ALIASES: Record<string, string> = { xlarge: "extra_large"
 
 const portalMedicalAlertSchema = z.object({
   id: z.string().optional(),
-  type: z.string(),
-  description: z.string(),
+  type: z.string().max(2000),
+  description: z.string().max(2000),
   severity: z.enum(["low", "medium", "high"]),
 });
 
@@ -275,12 +275,16 @@ const portalPetUpdateSchema = z.object({
   birthDate: z.string().nullable().optional(),
   notes: z.string().max(2000).nullable().optional(),
   healthAlerts: z.string().max(2000).nullable().optional(),
-  photoUrl: z.string().nullable().optional(),
+  // photoUrl/photoKey are intentionally NOT writable here: photoKey is a trusted
+  // S3 object key consumed server-side (getPresignedGetUrl / deleteObject), and the
+  // upload path (pets.ts) already enforces a pets/{petId}/ prefix guard against key
+  // hijacking. Photo changes go through the dedicated upload + /photo/confirm flow.
+  // The web form round-trips the GET-shaped photoUrl; Zod strips it as an unknown key.
   // coatType / petSizeCategory validated in-handler so bad values return 422.
   coatType: z.string().nullable().optional(),
   petSizeCategory: z.string().nullable().optional(),
-  preferredCuts: z.array(z.string()).nullable().optional(),
-  medicalAlerts: z.array(portalMedicalAlertSchema).nullable().optional(),
+  preferredCuts: z.array(z.string().max(2000)).max(50).nullable().optional(),
+  medicalAlerts: z.array(portalMedicalAlertSchema).max(50).nullable().optional(),
 });
 
 portalRouter.patch(
@@ -292,6 +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)
@@ -322,7 +334,8 @@ portalRouter.patch(
 
     if (body.notes !== undefined) updateData.groomingNotes = body.notes;
     if (body.healthAlerts !== undefined) updateData.healthAlerts = body.healthAlerts;
-    if (body.photoUrl !== undefined) updateData.photoKey = body.photoUrl;
+    // photoKey is intentionally not writable here — see portalPetUpdateSchema note.
+    // Photo changes go through the key-validated upload + /photo/confirm flow.
 
     if (body.coatType !== undefined) {
       if (body.coatType !== null && !PORTAL_COAT_TYPES.includes(body.coatType)) {
@@ -546,17 +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(
@@ -574,7 +603,7 @@ portalRouter.post(
         petId: body.petId,
         serviceId: body.serviceId,
         preferredDate: body.preferredDate,
-        preferredTime: body.preferredTime,
+        preferredTime: normalizeTime(body.preferredTime),
       })
       .returning();
 
@@ -605,7 +634,7 @@ 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 +1,284 @@
+import { Hono } 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,
+  type RouteStopInput,
+} from "../services/routeOptimization.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"),
+});
+
+/**
+ * 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));
+}
+
+/**
+ * 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);
+  return c.json({ route, stops });
+});
+
+/**
+ * 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),
+            bufferMins,
+          }))
+        );
+      }
+
+      return routeRow!;
+    });
+
+    const stops = await loadRouteStops(db, route.id);
+    return c.json({
+      route,
+      stops,
+      provider: optimized.provider,
+      chunked: optimized.chunked,
+      subRouteCount: optimized.subRouteCount,
+      skipped,
+      warnings,
+    });
+  }
+);

src/services/routeOptimization.ts

@@ -0,0 +1,413 @@
+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;
+}