Connect Multiple Email Accounts to ChatGPT Work
ChatGPT Work’s apps hold one Gmail and one Outlook at a time, and never two of either, but a Work run can still reach every mailbox you own. Connect each account to Carly, add Carly to Work once, and a single run works across all of them at once, Gmail and Outlook.
1. Add your Gmail and Outlook mailboxes to Carly
- Sign in at carlyassistant.com.
- Open carlyassistant.com/integrations.
- Find Gmail and Outlook, click Connect, and authorize the mailbox.
- Click Connect again for the next one, and keep going for as many mailboxes as you want.
A Google Workspace or Microsoft 365 account may need administrator review. Ask the administrator to approve, then finish authorization.
Mix providers freely here. This is the step ChatGPT Work’s own connectors cannot do: a second Gmail sits beside the first, and Outlook sits beside both.
Carly connects to thousands of apps, so while you are on that page you can add your calendars, files, CRM, and anything else you want ChatGPT Work to reach through the same connector.
2. Add Carly to ChatGPT Work
- Open Plugins in the sidebar.
- Click +.
- Paste
https://carlyassistant.com/mcp/. - Continue to authorization.
- Sign in to the Carly account holding your mailboxes.
- Make Carly available to the session.
OpenAI's app directory became a plugin directory on July 9, 2026, shared between ChatGPT and Codex. Plugins are packages that can carry apps, skills, or app templates. It is a repackaging of how things are listed and discovered, not a change to the MCP plumbing underneath.
If + is greyed out on a Business or Enterprise workspace, the administrator may need to enable the plugin first.
What one session can do afterwards
- Search a personal Gmail and a work Outlook in the same question.
- Compare a thread in one company’s mailbox against another’s.
- Produce a morning briefing grouped by inbox.
- Draft or send from any of your addresses.
- Label, move, flag or archive in any of your accounts.
- Check all your calendars for conflicts before booking anything.
- Work a team inbox such as
billing@that belongs to the company, not to your login.
Why one connector cannot hold both
ChatGPT has held several Google accounts since August 2026, and on September 17, 2026 OpenAI said the same now works on plugins beyond Gmail, Calendar and Contacts, on every plan. What it did not publish is the list: which plugins took the update and how many accounts each one holds, so the honest test is the gear icon on each connection. Carly holds all of them at once, across thousands of apps.
ChatGPT Work’s own connectors versus Carly
| ChatGPT Work’s Gmail and Outlook | Carly | |
|---|---|---|
| Gmail accounts at once | One | Every one you connect |
| Outlook accounts at once | One | Every one you connect |
| Gmail and Outlook together | Yes, one of each | Yes, any number of each |
| Sends with attachments | No | Yes |
| Starts when mail arrives | No | Yes |
ChatGPT drafts and sends from a connected Gmail or Outlook account, with you confirming each send. Claude sends too: its Gmail connector drafts, sends, replies and forwards, and its Microsoft 365 connector does the same once an admin enables the write tools, though that one rejects anything with an attachment. Both need you in the conversation. Carly sends the reply while you are away, attachments included.
Carly’s agents also carry their own name, email address and memory, so a colleague or client can write to one directly and the work begins on arrival rather than when you next open a session. Around the mail, Carly connects to thousands of apps. Free Zapier-style workflows; AI agents from $35/month.
Connect every inbox at carlyassistant.com.
Quick fixes when a mailbox does not appear
- The provider reused your signed-in account. Choose Use another account on the provider’s screen rather than the suggested profile.
- A work account stalls at consent. A Google Workspace or Microsoft 365 administrator has to approve before authorization completes.
- ChatGPT Work does not see Carly. Reopen Plugins and confirm Carly is enabled for the current run.
Frequently asked questions
What about a shared mailbox like billing@?
On a company workspace this is usually where it bites: the mailbox belongs to the team, not to the account signed in to Work, and attachments in a shared mailbox do not come back through the native app. Carly holds it as a mailbox in its own right, so a Work task can just check the billing inbox. See Can ChatGPT access a shared mailbox?.
Can ChatGPT Work connect to multiple email accounts?
Its own apps hold one Gmail and one Outlook at a time. Connecting every mailbox to Carly and adding Carly to Work once lets a single run reach all of them.
Can ChatGPT Work connect two Gmail accounts?
Not through its own apps, which authorize a single Google account and replace it when you sign in with a second. Carly holds both at once.
Can ChatGPT Work read a shared Outlook mailbox?
Yes. Pass the mailbox owner’s address and Work can read, file and send plain-text mail from a shared or delegated mailbox your account can already open.
Does switching accounts give me both inboxes?
No. Connected apps are scoped per login, so no single run reaches across them.
More: ChatGPT Work with multiple accounts · How to connect multiple Gmail accounts to ChatGPT Work · How to connect multiple Outlook accounts to ChatGPT Work · ChatGPT Work and email · Best AI assistants for multiple email accounts
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