Resolve Orin's Gmail to the real google-calendar-orin Dapier connection and name connection and account when it is missing

backend/src/sponsorDocs/emailDelivery.ts

@@ -10,8 +10,7 @@
  * 2. DataOps reads the machine credential `personal-scheduler.dapier-api-token`
  *    and exchanges it at `POST https://dapier.dtcdev.click/api/agent/token`
  *    for a short-lived Google access token on Orin's Dapier connection
- *    (`gmail-orin` or `DATAOPS_ORIN_GMAIL_CONNECTION_ID`), kept separate from
- *    the calendar connection so Gmail send scope does not widen calendar grants.
+ *    (`google-calendar-orin` or `DATAOPS_ORIN_GMAIL_CONNECTION_ID`).
  * 3. DataOps verifies that the Dapier connection is bound to
  *    `orin@datatalks.club` before sending, then posts a raw RFC 2822 MIME
  *    message to `POST https://gmail.googleapis.com/gmail/v1/users/me/messages/send`.
@@ -40,8 +39,8 @@ import {
 
 export const SPONSOR_DOC_EMAIL_FROM = 'orin@datatalks.club';
 export const SPONSOR_DOC_EMAIL_CC = 'valeriia@datatalks.club';
-export const DEFAULT_ORIN_GMAIL_CONNECTION_ID = 'gmail-orin';
-export const DEDICATED_ORIN_GMAIL_CONNECTION_ID = 'gmail-orin';
+/** Orin's Gmail grants live on her Google connection in Dapier (the one that also holds calendar). */
+export const DEFAULT_ORIN_GMAIL_CONNECTION_ID = 'google-calendar-orin';
 
 const GMAIL_API_BASE = 'https://gmail.googleapis.com/gmail/v1/users/me';
 const GOOGLE_USERINFO_URL = 'https://www.googleapis.com/oauth2/v3/userinfo';
@@ -212,7 +211,7 @@ function summarizeGmailError(status: number, bodyText: string, connectionId: str
       `Gmail API returned HTTP 403${detail ? ` (${detail})` : ''}. `
       + `Dapier connection "${connectionId}" (${SPONSOR_DOC_EMAIL_FROM}) needs the `
       + `https://www.googleapis.com/auth/gmail.send scope granted and re-consented in Dapier `
-      + `(or connect "${DEDICATED_ORIN_GMAIL_CONNECTION_ID}" as ${SPONSOR_DOC_EMAIL_FROM}).`
+      + `(set DATAOPS_ORIN_GMAIL_CONNECTION_ID to the Dapier connection holding ${SPONSOR_DOC_EMAIL_FROM}).`
     );
   }
   return `Gmail API returned HTTP ${status}${detail ? `: ${detail}` : ''}.`;

backend/src/sponsorDocs/gmailMessageRoute.ts

@@ -38,7 +38,13 @@ export async function resolveGmailMessageRoute(
     body: JSON.stringify({ connection_id: connectionId, agent: DAPIER_AGENT }),
     signal: AbortSignal.timeout(10000),
   }).catch(() => null);
-  if (!tokenRes?.ok) throw new GmailMessageRouteError(`The Dapier broker refused the Gmail token for connection "${connectionId}" (HTTP ${tokenRes?.status ?? 'unreachable'}).`);
+  if (tokenRes?.status === 404) {
+    throw new GmailMessageRouteError(
+      `Dapier has no connection "${connectionId}" for ${SPONSOR_DOC_EMAIL_FROM}. Expected the Dapier connection holding that account's Gmail `
+      + `(default "${DEFAULT_ORIN_GMAIL_CONNECTION_ID}"); set DATAOPS_ORIN_GMAIL_CONNECTION_ID to the right connection id.`,
+    );
+  }
+  if (!tokenRes?.ok) throw new GmailMessageRouteError(`The Dapier broker refused the Gmail token for connection "${connectionId}" (${SPONSOR_DOC_EMAIL_FROM}) (HTTP ${tokenRes?.status ?? 'unreachable'}).`);
   const token = (await tokenRes.json().catch(() => ({}))) as { access_token?: string; provider_account_id?: string };
   if (!token.access_token) throw new GmailMessageRouteError(`Dapier connection "${connectionId}" returned no access token.`);
   if (String(token.provider_account_id || '').toLowerCase() !== SPONSOR_DOC_EMAIL_FROM) {

backend/tests/gmail-message-route.test.ts

@@ -0,0 +1,42 @@
+import assert from 'node:assert/strict';
+import { afterEach, test } from 'node:test';
+
+import { GmailMessageRouteError, resolveGmailMessageRoute } from '../src/sponsorDocs/gmailMessageRoute';
+
+const saved = process.env.DATAOPS_ORIN_GMAIL_CONNECTION_ID;
+afterEach(() => {
+  if (saved === undefined) delete process.env.DATAOPS_ORIN_GMAIL_CONNECTION_ID;
+  else process.env.DATAOPS_ORIN_GMAIL_CONNECTION_ID = saved;
+});
+
+test('Orin Gmail route resolves through the real google-calendar-orin connection', async () => {
+  delete process.env.DATAOPS_ORIN_GMAIL_CONNECTION_ID;
+  const requested: string[] = [];
+  const fetchImpl = (async (url: string, init?: RequestInit) => {
+    if (String(url).endsWith('/api/agent/token')) {
+      requested.push(JSON.parse(String(init?.body)).connection_id);
+      return Response.json({ access_token: 't', provider_account_id: 'orin@datatalks.club' });
+    }
+    return Response.json({
+      threadId: 'th1',
+      payload: { headers: [
+        { name: 'From', value: 'Orin <orin@datatalks.club>' },
+        { name: 'To', value: 'Sponsor <s@example.com>' },
+      ] },
+    });
+  }) as unknown as typeof fetch;
+  const route = await resolveGmailMessageRoute('m1', { fetchImpl, credential: 'c' });
+  assert.deepEqual(requested, ['google-calendar-orin']);
+  assert.equal(route.threadRef, 'th1');
+});
+
+test('a missing Dapier connection names the connection and account', async () => {
+  const fetchImpl = (async () => new Response('{}', { status: 404 })) as unknown as typeof fetch;
+  await assert.rejects(
+    resolveGmailMessageRoute('m1', { fetchImpl, credential: 'c' }),
+    (error: unknown) => error instanceof GmailMessageRouteError
+      && /no connection "google-calendar-orin"/.test(error.message)
+      && /orin@datatalks\.club/.test(error.message)
+      && /DATAOPS_ORIN_GMAIL_CONNECTION_ID/.test(error.message),
+  );
+});

backend/tests/sponsor-docs.test.ts

@@ -683,7 +683,7 @@ describe('Sponsor Content Docs API (/api/sponsor-docs)', () => {
                 access_token: 'ya29.orin-gmail-access-token',
                 expires_in: 3600,
                 token_type: 'Bearer',
-                connection_id: 'gmail-orin',
+                connection_id: 'google-calendar-orin',
               }),
               { status: 200, headers: { 'Content-Type': 'application/json' } },
             );
@@ -731,7 +731,7 @@ describe('Sponsor Content Docs API (/api/sponsor-docs)', () => {
       assert.strictEqual(created.emailDelivery?.taskId, ownerTask.id);
       assert.match(created.emailDelivery?.subject || '', /^ClickHouse \+ DataTalks\.Club Newsletter - 11-16-2026$/);
       assert.strictEqual(created.doc.emailDelivery?.state, 'sent');
-      assert.deepEqual(requestedConnections, ['gmail-orin'], 'the dedicated send connection cannot be overridden by the API request');
+      assert.deepEqual(requestedConnections, ['google-calendar-orin'], 'the dedicated send connection cannot be overridden by the API request');
       const taskAfterCreate = await getTask(client, ownerTask.id);
       assert.match(taskAfterCreate?.notesLog?.[0]?.text || '', /gmail-msg-orin-1/);
       assert.equal(taskAfterCreate?.taskHistory.at(-1)?.action, 'noted');
@@ -819,7 +819,7 @@ describe('Sponsor Content Docs API (/api/sponsor-docs)', () => {
       assert.strictEqual(retried.emailDelivery?.state, 'deferred');
       assert.strictEqual(retried.emailDelivery?.reason, 'insufficient_gmail_scope');
       assert.match(retried.emailDelivery?.message || '', /gmail\.send/);
-      assert.strictEqual(retryConnection, 'gmail-orin', 'the send-email API also pins the dedicated connection');
+      assert.strictEqual(retryConnection, 'google-calendar-orin', 'the send-email API also pins the dedicated connection');
 
       // Verify the dedicated gmail-orin connection sends after the prior scope failure.
       setSponsorDocEmailDepsForTests({
@@ -832,7 +832,7 @@ describe('Sponsor Content Docs API (/api/sponsor-docs)', () => {
             const connId = reqBody.connection_id || '';
             return new Response(
               JSON.stringify({
-                access_token: connId === 'gmail-orin' ? 'ya29.orin-dedicated-gmail' : 'ya29.orin-calendar-only',
+                access_token: connId === 'google-calendar-orin' ? 'ya29.orin-dedicated-gmail' : 'ya29.orin-calendar-only',
                 expires_in: 3600,
                 provider_account_id: 'orin@datatalks.club',
               }),
@@ -863,7 +863,7 @@ describe('Sponsor Content Docs API (/api/sponsor-docs)', () => {
       assert.strictEqual(fallbackRes.statusCode, 200, fallbackRes.body);
       const fallbackBody = JSON.parse(fallbackRes.body);
       assert.strictEqual(fallbackBody.emailDelivery?.state, 'sent');
-      assert.strictEqual(fallbackBody.emailDelivery?.connectionId, 'gmail-orin');
+      assert.strictEqual(fallbackBody.emailDelivery?.connectionId, 'google-calendar-orin');
       assert.strictEqual(fallbackBody.emailDelivery?.messageId, 'gmail-msg-orin-fallback');
       const taskAfterRetry = await getTask(client, ownerTask.id);
       assert.match(taskAfterRetry?.notesLog?.at(-1)?.text || '', /gmail-msg-orin-fallback/);