chore: move orgRole back to session

apps/api/src/app.ts

@@ -53,6 +53,7 @@ export const app = new Hono()
     if (isPublicCorsPath(c.req.path)) {
       c.set('user', null);
       c.set('session', null);
+      c.set('orgRoles', {});
 
       return next();
     }
@@ -68,6 +69,7 @@ export const app = new Hono()
     if (!session) {
       c.set('user', null);
       c.set('session', null);
+      c.set('orgRoles', {});
       await next();
 
       return;
@@ -75,6 +77,7 @@ export const app = new Hono()
 
     c.set('user', session.user);
     c.set('session', session.session);
+    c.set('orgRoles', (session as { orgRoles?: Record<string, number> }).orgRoles ?? {});
     await next();
   })
 

apps/api/src/middlewares/org-admin-or-automation-key.ts

@@ -3,7 +3,6 @@ import type { TOrganizationApiKeyScope } from '@cio/utils/validation/organizatio
 
 import { ErrorCodes } from '@api/utils/errors';
 import { ROLE } from '@cio/utils/constants';
-import { getOrgRolesForUser } from '@api/utils/redis/org-roles-cache';
 import { organizationApiKeyHasScopes } from '@api/services/organization/automation-key';
 
 export const orgAdminOrAutomationKeyMiddleware =
@@ -56,7 +55,7 @@ export const orgAdminOrAutomationKeyMiddleware =
         );
       }
 
-      const orgRoles = await getOrgRolesForUser(user.id);
+      const orgRoles = (c.get('orgRoles') as Record<string, number> | undefined) ?? {};
       if (orgRoles[orgId] !== ROLE.ADMIN) {
         return c.json(
           {

apps/api/src/middlewares/org-admin.ts

@@ -2,11 +2,11 @@ import { Context, Next } from 'hono';
 
 import { ErrorCodes } from '@api/utils/errors';
 import { ROLE } from '@cio/utils/constants';
-import { getOrgRolesForUser } from '@api/utils/redis/org-roles-cache';
 
 /**
  * Middleware to check if the authenticated user is an admin of the organization.
- * Reads `orgRoles` from the Redis-backed cache (DB fallback on miss).
+ * Reads the role from the Better Auth session (populated by the customSession plugin),
+ * so no per-request DB query is performed.
  *
  * Requires authMiddleware to be applied first.
  * Expects orgId in the 'cio-org-id' header.
@@ -37,7 +37,7 @@ export const orgAdminMiddleware = async (c: Context, next: Next) => {
       );
     }
 
-    const orgRoles = await getOrgRolesForUser(user.id);
+    const orgRoles = (c.get('orgRoles') as Record<string, number> | undefined) ?? {};
     const roleId = orgRoles[orgId];
 
     if (roleId !== ROLE.ADMIN) {

apps/api/src/middlewares/org-member.ts

@@ -1,11 +1,9 @@
 import { Context, Next } from 'hono';
-import { getOrgRolesForUser } from '@api/utils/redis/org-roles-cache';
 
 /**
  * Middleware to check if the authenticated user is a member of the organization.
- * Loads `orgRoles` from the Redis-backed cache (DB fallback on miss) so the
+ * Reads the role from the Better Auth session (populated by the customSession plugin),
- * lookup stays out of the Better Auth session cookie — keeping that cookie
+ * so no per-request DB query is performed.
- * small enough for the oauth-proxy redirect to fit in a Location header.
  *
  * Requires authMiddleware to be applied first.
  * Expects orgId in the 'cio-org-id' header.
@@ -37,7 +35,7 @@ export const orgMemberMiddleware = async (c: Context, next: Next) => {
       );
     }
 
-    const orgRoles = await getOrgRolesForUser(user.id);
+    const orgRoles = (c.get('orgRoles') as Record<string, number> | undefined) ?? {};
     const roleId = orgRoles[orgId];
 
     if (roleId === undefined) {

apps/api/src/types/auth.ts

@@ -6,6 +6,7 @@ export type AuthSession = {
     actorId: string | null;
     automationKey: TOrganizationApiKey | null;
     orgId: string | null;
+    orgRoles: Record<string, number>;
     session: typeof auth.$Infer.Session.session | null;
     user: typeof auth.$Infer.Session.user | null;
     userRole: number | null;

apps/api/src/utils/redis/org-roles-cache.ts

@@ -1,39 +0,0 @@
-import { getUserOrgRolesMap } from '@cio/db/queries/organization';
-import { logRedisUnavailableOnce, redis } from './redis';
-
-const TTL_SECONDS = 60 * 60; // 1 hour, matches the prior cookieCache.maxAge.
-
-const cacheKey = (userId: string) => `org-roles:${userId}`;
-
-export async function getOrgRolesForUser(userId: string): Promise<Record<string, number>> {
-  try {
-    const cached = await redis.get(cacheKey(userId));
-    if (cached) {
-      try {
-        return JSON.parse(cached) as Record<string, number>;
-      } catch {
-        // Stale/corrupt entry — fall through to DB.
-      }
-    }
-  } catch (error) {
-    logRedisUnavailableOnce('Redis GET org-roles failed, falling back to DB', error);
-  }
-
-  const orgRoles = await getUserOrgRolesMap(userId);
-
-  try {
-    await redis.set(cacheKey(userId), JSON.stringify(orgRoles), { EX: TTL_SECONDS });
-  } catch (error) {
-    logRedisUnavailableOnce('Redis SET org-roles failed, cache disabled', error);
-  }
-
-  return orgRoles;
-}
-
-export async function invalidateOrgRolesCache(userId: string): Promise<void> {
-  try {
-    await redis.del(cacheKey(userId));
-  } catch (error) {
-    logRedisUnavailableOnce('Redis DEL org-roles failed, falling back to TTL', error);
-  }
-}

packages/db/GOOGLE_AUTH.md

@@ -0,0 +1,167 @@
+# Google OAuth across multiple apex domains
+
+This doc explains how Google sign-in works for ClassroomIO across three different host families:
+
+- `app.classroomio.com` — admin dashboard
+- `<orgSiteName>.classroomio.school` — free-tier tenant sites
+- `<customer-owned>.com` — BYOD custom domains via Cloudflare for SaaS
+
+All three need to sign users in via Google, set host-only auth cookies on the originating host, and land the user back on the page they started from.
+
+## The problem
+
+Google OAuth requires every callback URL to be **registered ahead of time** in Google Cloud Console. Wildcards are not allowed in standard apps. We can't register `*.classroomio.school` or every BYOD customer's domain.
+
+We also can't share auth cookies across apex domains: a cookie on `api.classroomio.com` won't be sent to a request on `acme.classroomio.school`. Even setting `Domain=.classroomio.school` won't help — the OAuth callback always lands on `api.classroomio.com` per the registered URI, and that response can only set cookies for `api.classroomio.com`.
+
+## The architecture
+
+```
+acme.classroomio.school                         api.classroomio.com                 Google
+─────────────────────────                       ─────────────────────               ──────
+
+POST /proxy/api/auth/sign-in/social
+         │
+         ▼
+   Cloudflare Worker (apps/tenant-router)
+   ─── strips /proxy, forwards ─────────────▶  POST /api/auth/sign-in/social
+                                                       │
+                                                       │ oAuthProxy plugin sees
+                                                       │ currentURL ≠ productionURL,
+                                                       │ rewrites callbackURL to
+                                                       │   acme.classroomio.school/
+                                                       │     api/auth/oauth-proxy-callback
+                                                       │ and forces redirect_uri to
+                                                       │   api.classroomio.com/.../callback/google
+                                                       ▼
+                                              ◀───── 200 { url: google authorize URL } ─────────────
+   browser navigates to Google ────────────────────────────────────────────────────────────────▶
+                                                                                                  │
+                                                                                                  │ user
+                                                                                                  │ consents
+                                                                                                  │
+   ◀────────────────────────────────────────── 302 redirect_uri (api.classroomio.com/...) ───────
+                                                       │
+   GET /api/auth/callback/google?state=...&code=... ──▶│
+                                                       │
+                                                       │ oAuthProxy plugin: skipStateCookieCheck=true
+                                                       │ Better Auth: exchange code, create user,
+                                                       │              create session, set Set-Cookie
+                                                       │              for api host
+                                                       │ oAuthProxy after-middleware: encrypt all
+                                                       │              Set-Cookie content into URL
+                                                       │              location=…?cookies=<encrypted>
+                                                       │
+                                                       │ APP-LEVEL SWAP (apps/api/src/app.ts):
+                                                       │   stash encrypted cookies in Redis
+                                                       │   under a short token, rewrite location to
+                                                       │   …?token=<short>  (drops 10KB → ~150 bytes)
+                                                       ▼
+   ◀────────── 302 …/oauth-proxy-callback?callbackURL=…&token=<short> ────────────────────────
+   browser follows back to the tenant host
+         │
+         ▼
+   Cloudflare Worker forwards (via `/api/auth/*` carve-out, no /proxy prefix)
+         │
+   GET /api/auth/oauth-proxy-callback?callbackURL=…&token=<short>
+                                                       │
+                                                       │ APP-LEVEL SWAP (inbound):
+                                                       │   read token from Redis, restore
+                                                       │   ?cookies=<encrypted>, delete token
+                                                       │
+                                                       │ Better Auth oAuthProxy endpoint:
+                                                       │   decrypt the cookies blob,
+                                                       │   re-emit each Set-Cookie on this response
+                                                       │   (so the browser scopes them to the
+                                                       │   tenant host)
+                                                       ▼
+   ◀────────────────────────────────────── 302 to original callbackURL ──────────────────────────
+   browser lands on acme.classroomio.school/, logged in.
+```
+
+The same flow works for `app.classroomio.com` (the proxy-skip branch in `oAuthProxy` kicks in when `currentURL === productionURL`) and for BYOD domains (`learn.acme.com`) routed through Cloudflare for SaaS.
+
+## Pieces and where they live
+
+| Concern | File | Notes |
+|---|---|---|
+| Better Auth + `oAuthProxy` plugin registration | `packages/db/src/auth.ts` | `productionURL: CONSTANTS.BASE_URL` makes `api.classroomio.com` the canonical OAuth-callback URL. |
+| Auth endpoint mount in Hono | `apps/api/src/app.ts` (`/api/auth/*` handler) | Rewrites `request.url` from `X-Forwarded-Host`/`-Proto` so the plugin sees the tenant host the user actually visited. |
+| Cookies → token swap (outbound + inbound) | `apps/api/src/app.ts` (`/api/auth/*` handler) | Stashes the encrypted `cookies=…` blob in Redis under a short token, drops Location header from 10KB+ to ~150 bytes. |
+| Redis storage helpers | `apps/api/src/utils/redis/oauth-handoff.ts` | `storeHandoffPayload` (2-minute TTL) + `consumeHandoffPayload` (single-use, GET-and-DEL). |
+| Cloudflare Worker | `apps/tenant-router/src/index.ts` | Forwards `/proxy/*` → API (stripping prefix) and `/api/auth/*` → API (as-is, no strip), everything else → dashboard. |
+| Browser-side base URL | `apps/dashboard/src/lib/utils/services/api/index.ts` (`getRequestBaseUrl`) | Returns `${origin}/proxy` in the browser so auth cookies stay host-only. |
+| Browser-side auth client baseURL | `apps/dashboard/src/lib/utils/services/auth/client.ts` | `${origin}/proxy/api/auth` — Better Auth's client treats a baseURL with a path as the full auth root, so we encode the post-Worker-strip path here. |
+| Auto-enrollment after first signup | `packages/db/src/auth/hooks/tenant-provisioning.ts` | Resolves the tenant org from `cio-org-id` header (email signup) or `x-forwarded-host` (OAuth host). Idempotent membership insert. |
+| `customSession` plugin (adds `orgRoles` to session) | `packages/db/src/auth.ts` | Loads `{ [orgId]: roleId }` via `getUserOrgRolesMap` and ships it inside the `session_data` cookie cache. Org-scoped middlewares read it from `c.get('orgRoles')` — no per-request DB query. |
+
+## Why the Redis handoff exists
+
+Better Auth's `oAuthProxy` plugin handles cross-origin OAuth by encrypting **every Set-Cookie** the OAuth callback emits — `session_token`, `session_data`, `account_data`, `dontRememberToken` — into a single `cookies=<huge>` query parameter on the redirect URL. For ClassroomIO with `cookieCache.enabled: true` and `storeAccountCookie: true`, that blob hits ~5KB raw / ~10KB hex-encoded.
+
+Some hop between Render and the browser (Render's edge proxy, suspect HTTP header size limit) silently drops responses with a Location header that big — the API thinks it sent a 302, but the browser never receives one. The OAuth flow hangs.
+
+The Redis handoff sidesteps the size limit entirely:
+
+- Encrypted cookies blob → Redis, keyed by a 32-hex-char token.
+- Location header carries only the token (~150 bytes total URL).
+- Tenant-host endpoint reads token from Redis, restores the cookies query param, hands the request to Better Auth as-if-original.
+
+Single-use (GET-and-DEL on read) and 2-minute TTL keep the surface small.
+
+## Google Cloud Console settings
+
+You only ever need **one** OAuth client and **one** registered callback URI for unlimited tenants:
+
+- **Authorized JavaScript origins**: `https://api.classroomio.com`
+- **Authorized redirect URIs**: `https://api.classroomio.com/api/auth/callback/google`
+
+Do **not** add tenant subdomains, `*.classroomio.school`, or BYOD customer domains — Google rejects wildcards for standard apps and the `oAuthProxy` plugin handles the redirect to the original tenant host on its own.
+
+### Sensitive scopes warning
+
+If Google's consent screen warns users that the app is requesting "sensitive" or "restricted" scopes (like Drive) during sign-in, check **Google Cloud Console → OAuth consent screen → Scopes**. Sign-in only requests `email`, `profile`, `openid`. If `drive.readonly` is in the declared scopes list there, remove it. Drive access is requested separately via the in-app picker (`apps/dashboard/src/lib/utils/functions/google-drive-picker.ts`) using incremental authorization, so the consent prompt for it only appears when a user actually opens the Drive picker.
+
+## Required env vars
+
+On the **API** Render service:
+
+| Var | Value | Why |
+|---|---|---|
+| `BETTER_AUTH_SECRET` | random 32+ char string | Encrypts the oauth-proxy cookies blob and signs sessions. |
+| `PUBLIC_SERVER_URL` | `https://api.classroomio.com` | Better Auth's `baseURL` and the `oAuthProxy` plugin's `productionURL`. |
+| `GOOGLE_CLIENT_ID` / `GOOGLE_CLIENT_SECRET` | from Google Cloud Console | OAuth client credentials. |
+| `REDIS_URL` | Render Key Value internal URL | Required for the cookies-→-token handoff. Without it the handoff falls back to inline cookies and the OAuth flow breaks on tenant subdomains. |
+
+On the **dashboard** Render service:
+
+| Var | Value | Why |
+|---|---|---|
+| `HOST_HEADER` | `x-forwarded-host` | SvelteKit adapter-node reads the effective host from this so `event.url.host` is the tenant/admin host the user is on. |
+| `PROTOCOL_HEADER` | `x-forwarded-proto` | Same, for protocol. |
+| `PRIVATE_APP_HOST` | `classroomio.school` | Used by `getSubdomain` in `layout-setup.ts` to extract the org siteName. |
+| `PUBLIC_SERVER_URL` | `https://api.classroomio.com` | Used at runtime only as a fallback / for `authClient`'s SSR-time URL constructor; browser code uses `${origin}/proxy` via `getRequestBaseUrl`. |
+| `PRIVATE_SERVER_URL` | API's internal Render URL | Server-side dashboard → API calls bypass the public edge. |
+
+## Verifying the flow
+
+After any change, exercise the full sequence and check the API logs:
+
+```
+[auth-handler] POST /api/auth/sign-in/social → 200
+[auth-handler] GET /api/auth/callback/google → 302 location.length≈150
+[auth-handler] GET /api/auth/oauth-proxy-callback → 302 (to original callbackURL)
+```
+
+If `location.length` is in the thousands again, the cookies → token swap didn't fire (check Redis connectivity, or that the response Location actually contains `cookies=`).
+
+If the proxy-callback request never appears, the Worker's `/api/auth/*` carve-out isn't deployed (`pnpm --filter @cio/tenant-router deploy`).
+
+If you get `state_security_mismatch`, the `oAuthProxy` plugin didn't detect the proxied flow on the callback side — most likely the `X-Forwarded-Host` rewrite in `apps/api/src/app.ts` isn't running, so `currentURL` looked like the production URL.
+
+## Known gotchas
+
+- **`storeAccountCookie: true` is fine again** with the Redis handoff. The size of the cookies blob no longer matters; it just has to fit in a Redis value (which has no practical ceiling here).
+- **`customSession` is gone.** `orgRoles` is fetched per-request from Redis in `org-member`, `org-admin`, and `org-admin-or-automation-key` middlewares (DB on cache miss, 1-hour TTL). Anywhere that mutates `organizationmember` for an **existing** user should call `invalidateOrgRolesCache(userId)` so the role change is visible immediately instead of after the TTL.
+- **OAuth state cookie check is skipped** on the callback when the `oAuthProxy` plugin engages (`skipStateCookieCheck: true`). CSRF is still protected by the unguessable random state token stored in the DB (Better Auth's `verification` table) and the 10-minute expiry. This is the documented Better Auth mitigation.
+- **Render service name swap** — `cio-api.onrender.com` is the **dashboard** service, `cio-api-vymh.onrender.com` is the **API** service. Render doesn't allow renaming. See `apps/tenant-router/wrangler.toml` for the same warning.

packages/db/src/auth.ts

@@ -6,9 +6,11 @@ import { sendChangeEmailConfirmation, sendVerificationEmail } from './auth/email
 
 import { betterAuth } from 'better-auth/minimal';
 import { createProfileHook } from './auth/hooks/create-profile';
+import { customSession } from 'better-auth/plugins/custom-session';
 import { db } from '@db/drizzle';
 import { drizzleAdapter } from 'better-auth/adapters/drizzle';
 import { config as emailAndPassword } from './auth/email-password';
+import { getUserOrgRolesMap } from './queries/organization/organization';
 import { loginLink } from './auth/plugins/login-link';
 import { oAuthProxy } from 'better-auth/plugins/oauth-proxy';
 import { resolveTrustedBrowserOrigin } from './utils';
@@ -76,7 +78,8 @@ export const auth: ReturnType<typeof betterAuth> = betterAuth({
     user: {
       create: {
         after: async (user, ctx) => {
-          console.log('[auth] databaseHooks.user.create.after: running', { userId: user.id, ctx });
+          console.log('[auth] databaseHooks.user.create.after: running', { userId: user.id });
+
           const request =
             (ctx as { context?: { request?: Request }; request?: Request } | undefined)?.context?.request ??
             (ctx as { request?: Request } | undefined)?.request;
@@ -119,6 +122,20 @@ export const auth: ReturnType<typeof betterAuth> = betterAuth({
       productionURL: CONSTANTS.BASE_URL
     }),
     loginLink(),
-    tokenExchange()
+    tokenExchange(),
+    // Attaches the user's org memberships ({ [orgId]: roleId }) to the session
+    // so org-scoped middlewares can authorize without a per-request DB query.
+    // Refreshes when the session cookie cache expires (see session.cookieCache.maxAge).
+    customSession(async ({ user, session }) => {
+      let orgRoles: Record<string, number> = {};
+      try {
+        if (user?.id) {
+          orgRoles = await getUserOrgRolesMap(user.id);
+        }
+      } catch (error) {
+        console.error('customSession: failed to load orgRoles', error);
+      }
+      return { user, session, orgRoles };
+    })
   ]
 });