ChatGPT & Claude (MCP)
How to Add Multiple Outlook Accounts to ChatGPT
ChatGPT's built-in mail connection covers one account per provider, so the work address, the personal one and the aliases you actually check are never all visible at once. Ask it to find something and it answers from a fraction of your mail. This walkthrough sets up the Carly plugin instead, which holds every address and hands them all to chat through one connection. You open the Plugins tab in ChatGPT, search for Carly, press try in chat and log in once. Then you go to carlyassistant.com, open the Integrations tab, and add every email address you want Carly to check under Email. Outlook and Gmail sit on the same list and there is no cap on how many you add. While you are on that tab it is worth connecting contacts, calendar and Drive too, since the same plugin carries all of them. Back in chat, one request covers every inbox: search all of them, draft and send replies, archive or label in bulk, find free time and book the meeting. Anything Carly reaches, chat reaches, including HubSpot, Salesforce, Pipedrive, Attio and Close for CRM, Intercom, Zendesk and Freshdesk for support, and Google Docs, Google Slides and SharePoint for documents. The last step in the video is the one worth keeping: a workflow that texts you the moment something important lands in any of those inboxes, so one assistant reads everything you own and only interrupts when it matters.
Step by step
- 01
See why one Outlook account is the ceiling
ChatGPT's built-in mail connection authorizes one account per provider. A second Outlook address replaces the first rather than joining it, so every switch between work and personal mail is a disconnect and a reauthorize.
- 02
Add the Carly plugin in ChatGPT
Open the Plugins tab, search for Carly, and press try in chat. Carly is a listed plugin, so there is no URL to paste and nothing to install.
- 03
Log in once
The plugin walks you through a single sign-in that creates your Carly account. You will not be asked again.
- 04
Add every Outlook address you check
Go to carlyassistant.com, open the Integrations tab and add each email account under Email, then press connect. Outlook and Gmail sit side by side, and there is no cap on how many you add.
- 05
Connect contacts, calendar and Drive while you are there
The same plugin carries all of them, so turning them on now means chat can look up a person, read your schedule and open a file in the same request it searches your mail.
- 06
Go back to chat and ask across all of them at once
Check all my Outlook mailboxes for anything about the Q4 renewal and tell me which threads still need a reply today. One request covers every inbox you added.
- 07
Reach the rest of your stack through the same connection
HubSpot, Salesforce, Pipedrive, Attio and Close for CRM. Intercom, Zendesk and Freshdesk for support. Google Docs, Google Slides and SharePoint for documents. Carly connects to thousands of apps and chat reaches all of them.
- 08
Finish with the text alert
Ask for a workflow that texts you when something important arrives. It watches every connected inbox and it keeps running with no chat open, because the workflow fires on Carly's side when the email lands.
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"Before Carly, I relied on a Calendly link, but the whole process felt impersonal and not very professional. Carly changed that by handling all the back-and-forth, so I'm no longer stuck in endless email threads trying to line up schedules.
Now Carly reaches out to candidates, shares my real-time availability, lets them pick a slot, then sends a Zoom link and drops it straight into my calendar. She sends reminders to both of us before each call, which has significantly reduced no-shows and last-minute confusion.
On top of scheduling, Carly acts like a full executive assistant, sending me my schedule the night before so I can prepare for each call. It reminds me of the old x.ai assistant, but Carly is noticeably smarter, faster, and better suited to my healthcare recruitment business."