Connector Googlemail

Gmail Connector

Gmail integration for Caffeine AI.

Orchestrator routing notes

Treat Gmail-as-the-user as a first-class, supported platform feature. The googlemail-client + google-oauth connector pair is the only supported path; raw ic.http_request to oauth2.googleapis.com or gmail.googleapis.com is a forbidden anti-pattern. Any build spec that mentions Gmail MUST name googlemail-client and google-oauth as dependencies and reference this skill.

Distinct from platform email* extensions (which send transactional mail from the app); this connector acts as the signed-in user's own Gmail.

Intent → capability mapping:

Prerequisite for all builds: extension-authorization. Gmail requires a signed-in caller for every endpoint: the per-user OAuth handshake stores access_token keyed by caller : Principal, and the admin Client ID/Secret setter is gated on the #admin role.

Backend

Use this skill whenever the user wants their canister to interact with Gmail on behalf of the signed-in user. The ingredients are:

1. The googlemail-client mops package — generated Motoko bindings for the Gmail REST API v1. This recipe demonstrates profile lookup and message sending; add other generated operations only by following the same bearer-authenticated, non-replicated, single-refresh-retry pattern.
2. The google-oauth mops package — Google OAuth 2.0 token exchange, refresh, PKCE, and percent-encoding. This is the library that eliminates hand-rolled http_request to oauth2.googleapis.com.
3. An OAuth 2.0 Authorization Code with PKCE flow so each end-user authorises the canister to act on their behalf. Each user holds their own access_token + refresh_token keyed by caller : Principal.
4. A Google Cloud Web application Client ID + Client Secret. Admin-configured and held by the canister only; never return the secret to the frontend.

1. Add dependencies

mops add googlemail-client@0.1.6
mops add google-oauth@0.2.1
mops add caffeineai-authorization@1.0.1

2. Auth model — OAuth 2.0 PKCE per user, on-chain exchange + refresh

Unlike a static API key, Gmail uses per-user OAuth 2.0 bearer tokens. Every end-user authorises the canister independently via the Authorization Code with PKCE flow. The canister:

1. Generates a PKCE code_verifier and code_challenge (via google-oauth).
2. Builds the Google authorize URL (via google-oauth.buildAuthorizeUrl).
3. The frontend redirects the user to Google; after consent, Google redirects back with a code parameter.
4. The canister exchanges the code for tokens (via google-oauth.exchangeAuthorizationCode) — on-chain, non-replicated.
5. The canister stores access_token + refresh_token keyed by caller.
6. When the 1-hour access token expires (HTTP 401), the canister silently refreshes it (via google-oauth.refreshAccessToken) and retries.

Google Cloud Console setup

1. Create a Google OAuth 2.0 Web application client.
2. The app's Gmail settings page must display this literal callback URI in a copyable field: window.location.origin + "/connect/gmail" — for example, https://my-app.caffeine.xyz/connect/gmail. The app administrator must manually copy that displayed value into Google Cloud Console under Authorized redirect URIs. Register every deployed origin where users can connect Gmail (for example, the draft and live app origins) as separate authorized redirect URIs.
3. Enable only the Gmail scopes the app needs on the consent screen.
4. Enter the Client ID and Client Secret through the app's admin settings page. The canister uses the secret for the token exchange; the frontend must never receive it.

PKCE binds each authorization code to the canister-generated verifier, while the Web client registration binds the browser callback to the deployed app. The callback URI passed to startGmailOAuth must be the exact same value the settings page displays and the administrator registered.

OAuth scopes

Learn the connected address with OAuth.getUserEmail (OIDC userinfo), not gmail_users_getProfile. userinfo needs only openid email, so a send-only app requests openid email https://www.googleapis.com/auth/gmail.send and nothing more. gmail_users_getProfile requires the restricted gmail.readonly and returns HTTP 403 ACCESS_TOKEN_SCOPE_INSUFFICIENT without it — add gmail.readonly only when the app actually reads mail. When combining APIs (e.g. Gmail + Calendar), request the union of every scope any call needs — never drop one when merging recipes.

Storing tokens

The bearer never leaves the canister. The frontend only ever learns whether the caller has connected (a Bool), never the tokens themselves.

• A Map<Principal, GmailConnection> keyed by caller. Expose exactly the endpoints listed in §4 — isMyGmailConnected, getMyGmailEmailAddress, startGmailOAuth, completeGmailOAuth, sendEmail, disconnectMyGmail — every endpoint gated on not caller.isAnonymous(). Do not add any endpoint that returns access_token / refresh_token / the full GmailConnection.
• Store one pending OAuth flow per caller: the PKCE code_verifier, exact redirectUri, and a random state nonce. Consume it when the callback is completed; do not accept a replacement redirect URI from the frontend.

Google refresh tokens do NOT rotate

Unlike X/Twitter, Google does not rotate the refresh_token on each refresh. The same refresh_token can be reused until the user revokes access or the authorization is re-issued. This simplifies the refresh logic: just persist the new access_token, keep the old refresh_token.

3. is_replicated = ?false is REQUIRED

1. Security. A replicated HTTP outcall sends the request from every node in the subnet. Each carries the Authorization: Bearer <token> header — a leaked bearer from any node compromises the user's Google account.
2. Billing. Replicated outcalls produce N parallel API calls. The IC charges ~13× the cycles, and Google counts each toward quota.
3. Determinism. Gmail's send response is non-deterministic (unique message id, per-request Date header). Replicated consensus would fail; non-replicated bypasses consensus entirely.

→ Always: is_replicated = ?false on every Config.

4. Canonical layout

The default shape: admin Client ID/Secret + per-user OAuth. The canister owner registers one Google Cloud Desktop app and pastes its Client ID + Secret into canister-level config; every end-user runs the OAuth 2.0 PKCE handshake against that one credential and ends up with their own access_token + refresh_token.

The example spans four files:

• src/backend/main.mo — the actor: state + includes only.
• src/backend/mixins/gmail-config.mo — admin-gated Client ID + Secret.
• src/backend/mixins/gmail-messaging.mo — per-user OAuth + sendEmail.
• src/backend/lib/gmail.mo — googlemail-client + google-oauth glue.

import Map "mo:core/Map";
import Nat64 "mo:core/Nat64";
import Principal "mo:core/Principal";
import AccessControl "mo:caffeineai-authorization/access-control";
import MixinAuthorization "mo:caffeineai-authorization/MixinAuthorization";
import MixinGmailConfig "mixins/gmail-config";
import MixinGmailMessaging "mixins/gmail-messaging";
import LibGmail "lib/gmail";

actor {
  let accessControlState : AccessControl.AccessControlState;
  include MixinAuthorization(accessControlState, null);

  let gmailConfig : {
    var clientId : Text;
    var clientSecret : Text;
  };
  include MixinGmailConfig(accessControlState, gmailConfig);

  let gmailConnections : Map.Map<Principal, LibGmail.GmailConnection>;
  let pendingGmailFlows : Map.Map<Principal, LibGmail.PendingOAuth>;
  include MixinGmailMessaging(gmailConfig, gmailConnections, pendingGmailFlows);
};

The migration chain head:

import Map "mo:core/Map";
import AccessControl "mo:caffeineai-authorization/access-control";

module {
  type GmailConnection = {
    accessToken : Text;
    refreshToken : Text;
    emailAddress : Text;
  };

  type PendingOAuth = {
    codeVerifier : Text;
    redirectUri : Text;
    state : Text;
  };

  type NewActor = {
    accessControlState : AccessControl.AccessControlState;
    gmailConfig : { var clientId : Text; var clientSecret : Text };
    gmailConnections : Map.Map<Principal, GmailConnection>;
    pendingGmailFlows : Map.Map<Principal, PendingOAuth>;
  };

  public func migration(_old : {}) : NewActor {
    {
      accessControlState = AccessControl.initState();
      gmailConfig = { var clientId = ""; var clientSecret = "" };
      gmailConnections = Map.empty<Principal, GmailConnection>();
      pendingGmailFlows = Map.empty<Principal, PendingOAuth>();
    };
  };
};

import AccessControl "mo:caffeineai-authorization/access-control";
import Runtime "mo:core/Runtime";

mixin (
  accessControlState : AccessControl.AccessControlState,
  gmailConfig : { var clientId : Text; var clientSecret : Text },
) {
  public query func isGmailConfigured() : async Bool {
    gmailConfig.clientId.size() > 0;
  };

  public shared ({ caller }) func setGmailCredentials(clientId : Text, clientSecret : Text) : async () {
    if (not AccessControl.hasPermission(accessControlState, caller, #admin)) {
      Runtime.trap("Unauthorized: Only admins can set Gmail credentials");
    };
    gmailConfig.clientId := clientId;
    gmailConfig.clientSecret := clientSecret;
  };
};

import Map "mo:core/Map";
import Principal "mo:core/Principal";
import Runtime "mo:core/Runtime";
import LibGmail "../lib/gmail";

mixin (
  gmailConfig : { var clientId : Text; var clientSecret : Text },
  gmailConnections : Map.Map<Principal, LibGmail.GmailConnection>,
  pendingGmailFlows : Map.Map<Principal, LibGmail.PendingOAuth>,
) {
  public query ({ caller }) func isMyGmailConnected() : async Bool {
    Map.containsKey(gmailConnections, Principal.compare, caller);
  };

  public query ({ caller }) func getMyGmailEmailAddress() : async ?Text {
    if (caller.isAnonymous()) {
      Runtime.trap("Sign in to view your connected Gmail address");
    };
    switch (Map.get(gmailConnections, Principal.compare, caller)) {
      case (?connection) ?connection.emailAddress;
      case null null;
    };
  };

  public shared ({ caller }) func startGmailOAuth(redirectUri : Text) : async Text {
    if (caller.isAnonymous()) {
      Runtime.trap("Sign in to connect Gmail");
    };
    if (gmailConfig.clientId.size() == 0) {
      Runtime.trap("Gmail is not configured (admin must set credentials)");
    };
    await* LibGmail.startAuthorize(
      gmailConfig.clientId, redirectUri, caller, pendingGmailFlows,
    );
  };

  public shared ({ caller }) func completeGmailOAuth(code : Text, state : Text) : async () {
    if (caller.isAnonymous()) {
      Runtime.trap("Sign in to connect Gmail");
    };
    if (gmailConfig.clientId.size() == 0) {
      Runtime.trap("Gmail is not configured");
    };
    let ?pending = Map.get(pendingGmailFlows, Principal.compare, caller) else {
      Runtime.trap("No pending OAuth flow — call startGmailOAuth first");
    };
    if (state != pending.state) {
      Runtime.trap("OAuth state did not match the pending Gmail flow");
    };
    Map.remove(pendingGmailFlows, Principal.compare, caller);
    let connection = await* LibGmail.exchangeCode(
      gmailConfig.clientId, gmailConfig.clientSecret, code,
      pending.redirectUri, pending.codeVerifier,
    );
    Map.add(gmailConnections, Principal.compare, caller, connection);
  };

  public shared ({ caller }) func sendEmail(
    to : Text, subject : Text, body : Text,
  ) : async Text {
    if (caller.isAnonymous()) {
      Runtime.trap("Sign in to send email");
    };
    let ?connection = Map.get(gmailConnections, Principal.compare, caller) else {
      Runtime.trap("Connect your Gmail account first");
    };
    await* LibGmail.sendEmail(
      gmailConfig.clientId, gmailConfig.clientSecret, connection, caller,
      gmailConnections, to, subject, body,
    );
  };

  public shared ({ caller }) func disconnectMyGmail() : async () {
    if (caller.isAnonymous()) {
      Runtime.trap("Sign in to disconnect");
    };
    Map.remove(gmailConnections, Principal.compare, caller);
  };
};

import Error "mo:core/Error";
import Map "mo:core/Map";
import Nat64 "mo:core/Nat64";
import Principal "mo:core/Principal";
import Text "mo:core/Text";
import Runtime "mo:core/Runtime";
import OAuth "mo:google-oauth/OAuth";
import { gmail_users_messages_send } "mo:googlemail-client/Apis/UsersApi";
import { type Message; JSON = Message } "mo:googlemail-client/Models/Message";
import { defaultConfig; type Config } "mo:googlemail-client/Config";

module {
  public type GmailConnection = {
    accessToken : Text;
    refreshToken : Text;
    emailAddress : Text;
  };

  public type PendingOAuth = {
    codeVerifier : Text;
    redirectUri : Text;
    state : Text;
  };

  // Send-only: learn the address via OIDC userinfo (`openid email`), so no
  // `gmail.readonly`. Add `.../gmail.readonly` here ONLY if the app reads mail.
  let SCOPES : Text = "openid email https://www.googleapis.com/auth/gmail.send";

  func configForToken(token : Text) : Config {
    {
      defaultConfig with
      auth = ?#bearer(token);
      is_replicated = ?false;
      max_response_bytes = ?Nat64.fromNat(2_000_000);
    };
  };

  public func startAuthorize(
    clientId : Text, redirectUri : Text, caller : Principal,
    pendingFlows : Map.Map<Principal, PendingOAuth>,
  ) : async* Text {
    let codeVerifier = await OAuth.generateCodeVerifier();
    let state = await OAuth.generateCodeVerifier();
    Map.add(pendingFlows, Principal.compare, caller, {
      codeVerifier;
      redirectUri;
      state;
    });
    OAuth.buildAuthorizeUrl(clientId, redirectUri, SCOPES, state, OAuth.computeCodeChallenge(codeVerifier));
  };

  public func exchangeCode(
    clientId : Text, clientSecret : Text, code : Text,
    redirectUri : Text, codeVerifier : Text,
  ) : async* GmailConnection {
    let tokens = await OAuth.exchangeAuthorizationCode(clientId, clientSecret, code, redirectUri, codeVerifier);
    let accessToken = accessTokenOf(tokens, "Token exchange");
    let refreshToken = tokens.refreshToken
      ?? Runtime.trap("Token exchange failed: missing refresh_token");
    // Learn the connected address via OIDC userinfo — needs only `openid email`,
    // never `gmail.readonly`. (If the app also reads mail and requests
    // `gmail.readonly`, `gmail_users_getProfile` is an equivalent alternative.)
    let emailAddress = (await OAuth.getUserEmail(accessToken))
      ?? Runtime.trap("Failed to fetch connected email from userinfo");
    { accessToken; refreshToken; emailAddress };
  };

  /// Send an email. On HTTP 401, refreshes the access token once and retries.
  /// Persists the refreshed token into `gmailConnections` keyed by `caller`.
  public func sendEmail(
    clientId : Text, clientSecret : Text, connection : GmailConnection,
    caller : Principal, gmailConnections : Map.Map<Principal, GmailConnection>,
    to : Text, subject : Text, body : Text,
  ) : async* Text {
    let rawMessage = "To: " # to # "\r\n"
      # "Subject: " # subject # "\r\n"
      # "Content-Type: text/plain; charset=UTF-8\r\n\r\n" # body;
    let message : Message = { Message.init {} with raw = ?rawMessage.encodeUtf8() };
    try {
      messageIdOf(await* gmail_users_messages_send(
        configForToken(connection.accessToken), "me", #_1_, "", #json, "", "", "", "", true, "", "", "", message,
      ));
    } catch e {
      let msg = e.message();
      if (not (msg.contains(#text("401")) or msg.contains(#text("Unauthorized")))) {
        Runtime.trap("Gmail send failed: " # msg);
      };
      let refreshed = await OAuth.refreshAccessToken(clientId, clientSecret, connection.refreshToken);
      let newToken = accessTokenOf(refreshed, "Token refresh");
      Map.add(gmailConnections, Principal.compare, caller, {
        connection with accessToken = newToken;
      });
      messageIdOf(await* gmail_users_messages_send(
        configForToken(newToken), "me", #_1_, "", #json, "", "", "", "", true, "", "", "", message,
      ));
    };
  };

  func accessTokenOf(tokens : OAuth.TokenResponse, operation : Text) : Text {
    switch (tokens.error) {
      case (?error) {
        let description = switch (tokens.errorDescription) {
          case (?value) ": " # value;
          case null "";
        };
        Runtime.trap(operation # " failed: " # error # description);
      };
      case null {};
    };
    tokens.accessToken ?? Runtime.trap(operation # " failed: missing access_token");
  };

  func messageIdOf(result : Message) : Text = result.id ?? "";
};

5. Available API surface

google-oauth (OAuth 2.0 mechanics)

googlemail-client (Gmail REST API)

The canonical actor above intentionally implements only profile lookup and message sending. For another generated operation, keep bearer authentication and is_replicated = ?false, then apply the same single-refresh-retry pattern as sendEmail.

6. Cycles and response sizes

The google-oauth library uses Call.httpRequest from mo:ic/Call, which auto-computes and attaches the exact required cycles via the ic0.cost_http_request system API. No manual cycle budgeting is needed for token exchange or refresh calls.

For googlemail-client calls, defaultConfig.cycles = 30_000_000_000 (30B). A typical send costs ~10–15B cycles. Bump to 60B for large messages. Set max_response_bytes = ?2_000_000 for message reads that may include large payloads.

7. Things that will bite you

• is_replicated = ?false — see §3. Non-negotiable.
• Google refresh tokens do NOT rotate. Unlike X/Twitter, Google does not issue a new refresh_token on each refresh. Keep the original refresh_token and only persist the new access_token. The sendEmail function in §4 handles this.
• Access tokens expire in 1 hour. The sendEmail function catches HTTP 401, silently refreshes via google-oauth.refreshAccessToken, and retries once. If the refresh also fails, surface "re-connect your account".
• Callback URI exact-match. Every character (trailing slash, query string, port) must match between the authorize URL and the redirect. Google returns redirect_uri_mismatch otherwise. Use the fixed window.location.origin + "/connect/gmail" for redirectUri — the same value the settings page displays and the /connect/gmail route owns — and register that exact URI on the Google Web client. Do not build it from window.location.pathname, which varies by page.
• Pass the displayed value to startGmailOAuth unchanged — never the raw *.icp0.io canister URL. A Caffeine app is served at several origins (the *-draft.caffeine.xyz draft, the *.caffeine.xyz live domain, and the raw <canister-id>.icp0.io URL). Compute the redirect URI in one shared helper (window.location.origin + "/connect/gmail") and use that same helper both for the copyable field on the settings page and for the value handed to startGmailOAuth. If the value sent to Google (via startGmailOAuth) differs from what the settings page showed and the admin registered — e.g. a build-time/config value or the *.icp0.io canister origin — Google returns redirect_uri_mismatch.
• RFC 5322 raw Blob. Pass the message as a plain Blob in the raw field (?Text.encodeUtf8(mime)). The googlemail-client base64-encodes it for the API — do not base64-encode it yourself (that double-encodes and Gmail rejects it).
• HTTP 429 rate-limit. Surface the error to the caller; never silently retry inside the canister — a send retry may deliver duplicates.
• Don't expose the access token. gmailConnections is read only by Map.get(gmailConnections, ..., caller) inside sendEmail. No getMyGmailConnection, no getMyAccessToken, no iterator. A leaked bearer is a per-user account compromise.
• xgafv = #_1_, alt = #json for all Gmail API v1 calls. Leave optional string parameters "" and prettyPrint = false.
• API query parameters are plain positional values, not ?T — never pass null for one. The client's function parameters are Text / Bool / enum (e.g. xgafv, alt, fields, prettyPrint); pass #_1_, #json, "", false — null will not type-check. Only model values (Message) are optional ?T.
• userId = "me" refers to the authenticated user.

Frontend

Every build using this skill MUST ship all four items below. (If the app also uses the Google Calendar connector, follow "Combined Gmail + Calendar apps" below instead — it replaces /settings/gmail + /connect/gmail with one shared /settings/google + /connect/google. The requirements below still apply; only the two paths change.) These are acceptance criteria, not suggestions — verify each before the build is done. These three are the requirements builds skip, and any one missing makes the connector broken, not merely incomplete:

• The credentials page exists and is reachable. The app MUST have the /settings/gmail page with Client ID/Secret inputs (item 2), and a signed-in admin MUST be able to reach it — via a nav link or the not-configured prompt on the connect page. A "Connect Gmail" button with no page to enter credentials is the most common failure and leaves the connector unusable.
• The admin settings page displays the literal, copyable redirect URI. Not a <your-domain> placeholder, not "your app URL + /connect/gmail" as text for the admin to assemble — the actual string window.location.origin + "/connect/gmail" rendered in a read-only field the admin can copy. Concretely: an app served from https://my-app.caffeine.xyz must show a field containing exactly https://my-app.caffeine.xyz/connect/gmail and nothing else. Without it the admin cannot register the URI in Google and every connection fails.
• /connect/gmail is a real route that handles Google's callback — not a button-only page. If it falls through to a catch-all/home redirect, or calls completeGmailOAuth before the authenticated actor is ready, the connection silently fails and the app shows "not connected".

1. A login flow — required. Gmail cannot work without a non-anonymous caller; the per-user OAuth handshake stores tokens keyed by caller : Principal, and the admin credential setter gates on #admin. The login flow comes from extension-authorization: useInternetIdentity, login/logout buttons, the useActor plumbing that injects the authenticated identity into every backend call.

2. An admin settings page — /settings/gmail (admin-gated). This page is required; a Gmail build is incomplete without it:

   • Show a "How to get your Google credentials" panel before the credential inputs. Reassure the admin it is a one-time, ~5-minute setup, and walk through these numbered steps (the agent's completion message must repeat the same steps):
     1. open the Google Cloud Console and sign in with any Google account;
     2. create or pick a project;
     3. enable the Gmail API (APIs & Services → Library → search "Gmail API" → Enable);
     4. configure the OAuth consent screen (APIs & Services → OAuth consent screen → External; set app name, support email, developer email; Google's default scopes are fine);
     5. create an OAuth client ID of type Web application (APIs & Services → Credentials → Create Credentials → OAuth client ID);
     6. under Authorized redirect URIs, add the exact value from the copyable field on this page;
     7. copy the resulting Client ID and Client Secret into the inputs below and save. Include a convenience link that opens the Google Cloud Console.
   • Render the actual URI in a read-only, copyable field using one shared helper: const gmailRedirectUri = () => window.location.origin + "/connect/gmail";. For example, if the app is open at https://my-app.caffeine.xyz, the displayed value is https://my-app.caffeine.xyz/connect/gmail. Never show only <app-domain> or ask the administrator to infer the URI.
   • Two password-inputs bound to setGmailCredentials(clientId, clientSecret). Submit on enter; clear inputs on success.
   • Status indicator driven by isGmailConfigured() (returns Bool). Show "Configured" / "Not configured" — never display the credentials.
   • Make this page reachable. The app's main navigation (the shared Layout) MUST link to this page for admins — show the link when isCallerAdmin is true, hide it otherwise (via extension-authorization). Add that link wherever the nav is defined, not inside this page. A /settings/gmail route with no way to reach it is a broken build. Do not rely on the nav alone: the not-configured prompt below is the primary way users discover setup is needed.

3. A "Connect Gmail" and callback page — /connect/gmail (any signed-in user). This dedicated page must catch and handle Google's redirect after consent; it is not only a page with a connect button:

   • Handle the not-configured case for everyone. isGmailConfigured() is a public query (any signed-in user may call it). When it returns false, do not show a dead connect button. Admins see a link to /settings/gmail to enter credentials. Non-admins must see an explanation, not a dead end — e.g. "Gmail isn't set up yet — the app's administrator needs to add Google credentials in Settings." Enable the "Connect Gmail" button only once configured.
   • "Connect Gmail" button bound to startGmailOAuth(gmailRedirectUri()). Redirect the browser to the URL returned by the canister. Do not derive the callback from an arbitrary current pathname; the fixed /connect/gmail route and the settings-page URI must be identical.
   • Register /connect/gmail as a real application route. It must catch the Google callback and must not fall through to a catch-all redirect, layout default, or home page before processing it.
   • On the return leg, read error, code, and state from URLSearchParams. If error is present, show the failed/declined connection state and do not call the canister. Only when both code and state are present, call and await completeGmailOAuth(code, state) before navigating anywhere or clearing the URL. Keep a visible "Connecting Gmail…" state while it is pending. Do not replace the route, redirect to the home page, or discard the query parameters first — that loses the one-time code and leaves the user disconnected.
   • Wait for actor readiness before the one-time callback call. The page must wait for useInternetIdentity().isAuthenticated and useActor(createActor) to provide a non-null, non-fetching actor before calling completeGmailOAuth. Do not set a startedRef/one-shot guard until then: on first render the actor is often unavailable, and an "Actor not ready" failure otherwise consumes the only retry while the authorization code is still in the URL.
   • After either terminal path, call history.replaceState to remove the OAuth query parameters. This prevents a page refresh from reusing a one-time authorization code.
   • Status driven by isMyGmailConnected() (returns Bool). When connected, call getMyGmailEmailAddress() to show "Connected as user@email.com". This returns only the stored email address, never either bearer token.
   • Optional "Disconnect Gmail" button bound to disconnectMyGmail().

4. Empty-state nudges. When isMyGmailConnected() is false, render an inline "Connect Gmail to send" link to /connect/gmail on the send-email UI. When isGmailConfigured() is false and the caller is an admin, render a "Set up Gmail" link to /settings/gmail so the credentials page is discoverable, not just reachable.

Suggested route layout:

/                   →  Main UI (any signed-in user; empty-state when no Gmail connection)
/settings/gmail     →  Admin credential config (admin-only)
/connect/gmail      →  Per-user OAuth handshake (any signed-in user)
# If the app ALSO uses Google Calendar: drop the two routes above and use a
# single /settings/google + /connect/google — see "Combined Gmail + Calendar apps".

Combined Gmail + Calendar apps

When an app uses both connectors, build one shared Google connection, not two (an auth code is single-use, so two flows would force two consent screens). Frontend:

• One admin page /settings/google — a single Client ID / Client Secret form, one isGoogleConfigured status, and one copyable redirect-URI field showing exactly window.location.origin + "/connect/google".
• One connect route /connect/google — the same real callback route the Frontend section above requires: it renders "Connect Google", catches the redirect, waits for actor readiness, then calls completion once. No second callback route.
• Do NOT build /settings/gmail, /connect/gmail, /settings/calendar, or /connect/calendar. Every other Frontend requirement above still applies — only these paths change.

Backend — write the shared flow once (it replaces both per-connector OAuth flows). It is the same shape as the per-connector startAuthorize / exchangeCode / refresh functions, with these exact differences:

• One #admin-gated config setter storing a single Client ID/Secret.
• SCOPES = the union below — both APIs in one consent.
• completeGoogleOAuth(code, state) learns the connected email via OAuth.getUserEmail (OIDC userinfo — needs only openid email, not gmail.readonly) and stores one connection { accessToken; refreshToken; emailAddress } in a single Map<Principal, GoogleConnection>.
• Gmail sends and Calendar calls each build their own client Config from that one accessToken, each keeping its single-refresh-on-401 retry.
• Keep the connection and client config in one shared state value and pass it as a parameter to both the Gmail and Calendar mixins, so both read and write the same connection (see the writing-motoko mixins rule).

let SCOPES : Text =
  "openid email "                                    // learn the address via userinfo
  # "https://www.googleapis.com/auth/gmail.send "
  # "https://www.googleapis.com/auth/calendar";
// Add "https://www.googleapis.com/auth/gmail.readonly " ONLY if the app reads mail.

Wire it as one connection shared by both services — declare the config, connection map, and pending-flow map once and pass the same bindings to every mixin. The Gmail and Calendar messaging mixins do not declare their own config or connection; they receive the shared googleConfig and googleConnections (config is needed for the refresh-on-401 retry):

actor {
  let accessControlState : AccessControl.AccessControlState;
  include MixinAuthorization(accessControlState, null);

  // ONE shared credential + connection state for both services.
  let googleConfig : { var clientId : Text; var clientSecret : Text };
  let googleConnections : Map.Map<Principal, Google.Connection>;
  let pendingGoogleFlows : Map.Map<Principal, Google.PendingOAuth>;

  include MixinGoogleConfig(accessControlState, googleConfig);                    // setGoogleCredentials / isGoogleConfigured (#admin-gated setter)
  include MixinGoogleOAuth(googleConfig, googleConnections, pendingGoogleFlows);  // startGoogleOAuth / completeGoogleOAuth, SCOPES = union above
  include MixinGmailMessaging(googleConfig, googleConnections);                  // sendEmail — refresh-on-401 needs config; reads the shared connection
  include MixinCalendarMessaging(googleConfig, googleConnections);               // calendar calls — same shared config + connection
};

This variant's migration chain head replaces the per-connector one:

import Map "mo:core/Map";
import AccessControl "mo:caffeineai-authorization/access-control";

module {
  type Connection = {
    accessToken : Text;
    refreshToken : Text;
    emailAddress : Text;
  };

  type PendingOAuth = {
    codeVerifier : Text;
    redirectUri : Text;
    state : Text;
  };

  type NewActor = {
    accessControlState : AccessControl.AccessControlState;
    googleConfig : { var clientId : Text; var clientSecret : Text };
    googleConnections : Map.Map<Principal, Connection>;
    pendingGoogleFlows : Map.Map<Principal, PendingOAuth>;
  };

  public func migration(_old : {}) : NewActor {
    {
      accessControlState = AccessControl.initState();
      googleConfig = { var clientId = ""; var clientSecret = "" };
      googleConnections = Map.empty<Principal, Connection>();
      pendingGoogleFlows = Map.empty<Principal, PendingOAuth>();
    };
  };
};

Do not give Gmail and Calendar separate config/connection state or separate OAuth flows — one auth code is single-use, and separate state desyncs (see the writing-motoko mixins rule).

Enable both APIs on the one OAuth client and register only the single .../connect/google redirect URI. Split into two separate panels only if the user explicitly asks to connect two different Google accounts.

Common to all variants

• Sign-in is required for every Gmail-related route. Wire the /settings/... and the connect route (/connect/gmail, or /connect/google in a combined app) through extension-authorization's auth guard (useInternetIdentity + redirect when !isAuthenticated).
• The frontend never persists tokens. No localStorage, no IndexedDB, no cookies — the canister mediates everything. The browser only ever sees Bool status flags and the OAuth redirect URLs.
• The OAuth state parameter is canister-generated and validated. The canister stores a random nonce with the pending verifier and callback URI. The frontend must pass both code and state to the completion call (completeGmailOAuth, or completeGoogleOAuth in a combined app); it never creates or modifies either value.
• The send-email UI itself is trivial: inputs for to, subject, body, a submit button. No client-side Gmail SDK, no token handling, no JSON serialization — the canister is the Gmail client.

Related

• mops add googlemail-client@0.1.6 — Gmail REST API bindings.
• mops add google-oauth@0.2.1 — Google OAuth 2.0 library (token exchange, refresh, PKCE, getUserEmail userinfo, DateTime RFC 3339 helpers).
• Google OAuth 2.0 for Web Server Applications — Web-client redirect URI and authorization-code flow reference.
• Gmail API v1 reference — what googlemail-client wraps.
• RFC 7636 — Proof Key for Code Exchange — PKCE spec.
• extension-authorization — required prerequisite. Provides Internet Identity login, useInternetIdentity / useActor frontend plumbing, and the #admin role gate.