sec: webhook SSRF guard, IMAP-sync owner check, watcher port membership

Three findings from a fourth-pass review:

1. MEDIUM — webhook URL SSRF. The validator only enforced HTTPS+URL
   parse; it accepted private/loopback/link-local/.internal hosts. The
   delivery worker fetched arbitrary URLs and persisted up to 1KB of
   response body into webhook_deliveries.response_body, which is then
   surfaced via the deliveries listing endpoint — a port admin could
   register a webhook to an internal HTTPS endpoint, hit the test
   endpoint to force immediate dispatch, and read the response back.
   Validator now rejects RFC-1918/loopback/link-local/CGNAT/ULA IPs
   (v4 + v6) and .internal/.local/.localhost/.lan/.intranet/.corp
   suffixes; the worker re-resolves the hostname at dispatch time and
   blocks before fetch (DNS rebinding defense). 21-case unit test
   covers the matrix.

2. MEDIUM — POST /api/v1/email/accounts/[id]/sync had no owner check.
   Any user with email:view could enqueue an inbox-sync job for any
   accountId, which the worker would honour using the foreign user's
   decrypted IMAP credentials and advance the account's lastSyncAt
   (data-loss risk on the legitimate owner's next sync). Route now
   asserts account.userId === ctx.userId before enqueueing, matching
   the toggle/disconnect endpoints.

3. MEDIUM — addDocumentWatcher (and the wizard / upload watcher
   inserts) didn't validate the watcher's userId belonged to the
   document's port. notifyDocumentEvent then emitted a real-time
   socket toast + email containing the document title to the foreign
   user. New assertWatchersInPort helper verifies each candidate has
   a userPortRoles row for the port (super-admin bypass).

818 vitest tests pass.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>

src/lib/queue/workers/webhooks.ts

@@ -1,9 +1,46 @@
 import { Worker, type Job } from 'bullmq';
 import { createHmac } from 'node:crypto';
+import { lookup } from 'node:dns/promises';
 
 import type { ConnectionOptions } from 'bullmq';
 import { logger } from '@/lib/logger';
 import { QUEUE_CONFIGS } from '@/lib/queue';
+import { isLocalOrPrivateHost } from '@/lib/validators/webhooks';
+
+/**
+ * Resolve the webhook hostname and reject if any returned address is in a
+ * disallowed range. Defends against DNS rebinding where the validator-time
+ * resolution returned a public address but dispatch-time resolution
+ * returns a private one.
+ */
+async function resolveAndCheckHost(
+  rawUrl: string,
+): Promise<{ ok: true } | { ok: false; reason: string }> {
+  if (isLocalOrPrivateHost(rawUrl)) {
+    return { ok: false, reason: 'webhook URL host blocked by static check' };
+  }
+  let host: string;
+  try {
+    host = new URL(rawUrl).hostname;
+  } catch {
+    return { ok: false, reason: 'invalid URL' };
+  }
+  try {
+    const addresses = await lookup(host, { all: true });
+    for (const a of addresses) {
+      // Reuse the validator's literal-address checks on each resolved IP.
+      if (isLocalOrPrivateHost(`https://${a.family === 6 ? `[${a.address}]` : a.address}`)) {
+        return { ok: false, reason: `resolved address ${a.address} is in a blocked range` };
+      }
+    }
+  } catch (err) {
+    return {
+      ok: false,
+      reason: `DNS resolution failed: ${err instanceof Error ? err.message : 'unknown'}`,
+    };
+  }
+  return { ok: true };
+}
 
 // ─── Job Payload ─────────────────────────────────────────────────────────────
 
@@ -27,8 +64,7 @@ export const webhooksWorker = new Worker(
       return;
     }
 
-    const { webhookId, portId, event, deliveryId, payload } =
-      job.data as WebhookDeliverPayload;
+    const { webhookId, portId, event, deliveryId, payload } = job.data as WebhookDeliverPayload;
 
     const { db } = await import('@/lib/db');
     const { webhooks, webhookDeliveries } = await import('@/lib/db/schema/system');
@@ -44,9 +80,7 @@ export const webhooksWorker = new Worker(
 
     if (!webhook) {
       logger.info({ webhookId }, 'Webhook deleted — skipping delivery');
-      await db
-        .delete(webhookDeliveries)
-        .where(eq(webhookDeliveries.id, deliveryId));
+      await db.delete(webhookDeliveries).where(eq(webhookDeliveries.id, deliveryId));
       return;
     }
 
@@ -82,6 +116,32 @@ export const webhooksWorker = new Worker(
     let responseBody: string | null = null;
     let success = false;
 
+    // SSRF gate: re-resolve the hostname at dispatch time and reject if it
+    // points anywhere internal. The validator already filtered literal
+    // hostnames at create/update time, but DNS rebinding could swap the
+    // answer between then and now.
+    const hostCheck = await resolveAndCheckHost(webhook.url);
+    if (!hostCheck.ok) {
+      logger.warn(
+        { webhookId, deliveryId, url: webhook.url, reason: hostCheck.reason },
+        'Webhook dispatch blocked by SSRF guard',
+      );
+      // Persist the failure so the deliveries listing reflects it.
+      const { db: dbInner } = await import('@/lib/db');
+      const { webhookDeliveries } = await import('@/lib/db/schema/system');
+      const { eq } = await import('drizzle-orm');
+      await dbInner
+        .update(webhookDeliveries)
+        .set({
+          status: 'dead_letter',
+          responseStatus: null,
+          responseBody: `Blocked: ${hostCheck.reason}`,
+          deliveredAt: new Date(),
+        })
+        .where(eq(webhookDeliveries.id, deliveryId));
+      return;
+    }
+
     try {
       const controller = new AbortController();
       const timeoutId = setTimeout(() => controller.abort(), 10_000);

src/lib/services/documents.service.ts

@@ -14,6 +14,7 @@ import { companies } from '@/lib/db/schema/companies';
 import { yachts } from '@/lib/db/schema/yachts';
 import { berthReservations } from '@/lib/db/schema/reservations';
 import { ports } from '@/lib/db/schema/ports';
+import { userProfiles, userPortRoles } from '@/lib/db/schema/users';
 import { buildListQuery } from '@/lib/db/query-builder';
 import { createAuditLog, type AuditMeta } from '@/lib/audit';
 import { diffEntity } from '@/lib/entity-diff';
@@ -337,6 +338,34 @@ async function assertSubjectFksInPort(
   await Promise.all(checks);
 }
 
+/**
+ * Reject watchers whose user does not have access to the document's port.
+ * Without this guard, a document watcher row could be created for a user
+ * outside the document's tenant; subsequent notifyDocumentEvent emits a
+ * socket toast + email to that user revealing the document's title.
+ * Super-admins are always allowed (they can watch anything).
+ */
+async function assertWatchersInPort(portId: string, userIds: string[]): Promise<void> {
+  if (userIds.length === 0) return;
+  const unique = [...new Set(userIds)];
+  // Super-admins bypass the port check.
+  const profiles = await db.query.userProfiles.findMany({
+    where: inArray(userProfiles.userId, unique),
+  });
+  const superAdmins = new Set(profiles.filter((p) => p.isSuperAdmin).map((p) => p.userId));
+  const needsCheck = unique.filter((u) => !superAdmins.has(u));
+  if (needsCheck.length === 0) return;
+  const roles = await db
+    .select({ userId: userPortRoles.userId })
+    .from(userPortRoles)
+    .where(and(inArray(userPortRoles.userId, needsCheck), eq(userPortRoles.portId, portId)));
+  const allowed = new Set(roles.map((r) => r.userId));
+  const denied = needsCheck.filter((u) => !allowed.has(u));
+  if (denied.length > 0) {
+    throw new ValidationError('One or more watchers do not have access to this port');
+  }
+}
+
 // ─── Create ───────────────────────────────────────────────────────────────────
 
 export async function createDocument(portId: string, data: CreateDocumentInput, meta: AuditMeta) {
@@ -1219,6 +1248,7 @@ export async function addDocumentWatcher(
   meta: AuditMeta,
 ): Promise<{ userId: string; addedAt: Date }> {
   await getDocumentById(documentId, portId);
+  await assertWatchersInPort(portId, [userId]);
   const [row] = await db
     .insert(documentWatchers)
     .values({ documentId, userId, addedBy: meta.userId })
@@ -1318,6 +1348,7 @@ export async function createFromWizard(
   if (!doc) throw new Error('Failed to insert document');
 
   if (data.watchers.length > 0) {
+    await assertWatchersInPort(portId, data.watchers);
     await db.insert(documentWatchers).values(
       data.watchers.map((userId) => ({
         documentId: doc.id,
@@ -1414,6 +1445,7 @@ export async function createFromUpload(
   );
 
   if (data.watchers.length > 0) {
+    await assertWatchersInPort(portId, data.watchers);
     await db.insert(documentWatchers).values(
       data.watchers.map((userId) => ({
         documentId: doc.id,

src/lib/validators/webhooks.ts

@@ -3,17 +3,101 @@ import { z } from 'zod';
 import { baseListQuerySchema } from '@/lib/api/route-helpers';
 import { WEBHOOK_EVENTS } from '@/lib/services/webhook-event-map';
 
+// ─── SSRF guards ──────────────────────────────────────────────────────────────
+
+const BLOCKED_HOSTNAME_SUFFIXES = [
+  '.internal',
+  '.local',
+  '.localhost',
+  '.lan',
+  '.intranet',
+  '.corp',
+  '.home',
+  '.private',
+];
+const BLOCKED_HOSTNAME_LITERALS = new Set([
+  'localhost',
+  '0.0.0.0',
+  '255.255.255.255',
+  // IPv6 metadata host (Azure/GCP); literal with brackets handled below
+  'metadata.google.internal',
+  'metadata.azure.internal',
+]);
+
+/** Returns true if `host` is an IPv4 address in any disallowed range. */
+function isBlockedIpv4(host: string): boolean {
+  const m = host.match(/^(\d{1,3})\.(\d{1,3})\.(\d{1,3})\.(\d{1,3})$/);
+  if (!m) return false;
+  const oct = m.slice(1, 5).map(Number);
+  if (oct.some((o) => o < 0 || o > 255)) return true; // malformed → treat as blocked
+  const [a, b] = oct as [number, number, number, number];
+  if (a === 10) return true; // 10/8 RFC1918
+  if (a === 127) return true; // 127/8 loopback
+  if (a === 169 && b === 254) return true; // 169.254/16 link-local + AWS IMDS
+  if (a === 172 && b >= 16 && b <= 31) return true; // 172.16/12 RFC1918
+  if (a === 192 && b === 168) return true; // 192.168/16 RFC1918
+  if (a === 100 && b >= 64 && b <= 127) return true; // 100.64/10 CGNAT
+  if (a === 0) return true; // 0/8 zero
+  if (a >= 224) return true; // multicast / reserved
+  return false;
+}
+
+/** Returns true if `host` is an IPv6 literal in any disallowed range. */
+function isBlockedIpv6(host: string): boolean {
+  // strip brackets if present
+  const h = host.replace(/^\[/, '').replace(/\]$/, '').toLowerCase();
+  if (h === '::1') return true; // loopback
+  if (h === '::') return true; // unspecified
+  if (h.startsWith('fe80:') || h.startsWith('fe80::')) return true; // link-local
+  if (/^f[cd][0-9a-f]{2}:/.test(h)) return true; // fc00::/7 unique-local
+  if (h.startsWith('::ffff:')) {
+    // IPv4-mapped — unwrap and check
+    const ipv4 = h.slice(7);
+    return isBlockedIpv4(ipv4);
+  }
+  return false;
+}
+
+/**
+ * Reject webhook URLs whose hostname targets a private/internal/loopback/
+ * link-local destination. The webhook worker `fetch`es the URL and writes
+ * a slice of the response body into `webhook_deliveries.response_body`,
+ * which is later returned by the deliveries listing endpoint — making any
+ * SSRF here an information-disclosure read primitive against any internal
+ * service the worker can reach. Does NOT defend against DNS rebinding;
+ * the worker performs its own re-resolution at dispatch time.
+ */
+export function isLocalOrPrivateHost(rawUrl: string): boolean {
+  let parsed: URL;
+  try {
+    parsed = new URL(rawUrl);
+  } catch {
+    return true;
+  }
+  const host = parsed.hostname.toLowerCase();
+  if (BLOCKED_HOSTNAME_LITERALS.has(host)) return true;
+  if (BLOCKED_HOSTNAME_SUFFIXES.some((s) => host === s.slice(1) || host.endsWith(s))) {
+    return true;
+  }
+  if (host.startsWith('[') || host.includes(':')) {
+    if (isBlockedIpv6(host)) return true;
+  }
+  if (isBlockedIpv4(host)) return true;
+  return false;
+}
+
+const urlSchema = z
+  .string()
+  .url('Must be a valid HTTPS URL')
+  .refine((u) => u.startsWith('https://'), 'Webhook URL must use HTTPS')
+  .refine((u) => !isLocalOrPrivateHost(u), 'Webhook URL host is not allowed');
+
 // ─── Create ───────────────────────────────────────────────────────────────────
 
 export const createWebhookSchema = z.object({
   name: z.string().min(1).max(200),
-  url: z.string().url('Must be a valid HTTPS URL').refine(
-    (u) => u.startsWith('https://'),
-    'Webhook URL must use HTTPS',
-  ),
-  events: z
-    .array(z.enum(WEBHOOK_EVENTS))
-    .min(1, 'At least one event must be selected'),
+  url: urlSchema,
+  events: z.array(z.enum(WEBHOOK_EVENTS)).min(1, 'At least one event must be selected'),
   isActive: z.boolean().default(true),
 });
 
@@ -21,11 +105,7 @@ export const createWebhookSchema = z.object({
 
 export const updateWebhookSchema = z.object({
   name: z.string().min(1).max(200).optional(),
-  url: z
-    .string()
-    .url('Must be a valid HTTPS URL')
-    .refine((u) => u.startsWith('https://'), 'Webhook URL must use HTTPS')
-    .optional(),
+  url: urlSchema.optional(),
   events: z.array(z.enum(WEBHOOK_EVENTS)).min(1).optional(),
   isActive: z.boolean().optional(),
 });