ChatGPT, Claude and Copilot for OutlookDrafts in your inbox.
A brief for every meeting.
Your AI assistant drafts replies in Outlook from your policies and records, and builds a brief for the next meeting on your calendar. Microsoft 365 teams can use ChatGPT, Claude or Copilot. Whichever you pick, a person sends every email.
Ask it like a colleague. Get an answer you can use.
“Prep me for my next meeting.”
You getA brief on who's coming: open deals, unpaid invoices, open tickets and a suggested agenda.
“Reply to the complaint about a wrong item.”
You getA draft in the thread, using your wrong-item policy and the order details.
“Write the follow-up from my 10am.”
You getA draft that recaps what was agreed and the next step, in your style.
“Which support emails are over a day old?”
You getUnanswered threads, each with a draft ready (daily digest add-on).
“Who handles refund disputes over $500?”
You getThe right person from your escalation list, and a handoff note.
“Where do we stand with this customer before I reply?”
You getPast orders, past tickets and the last few emails, in a few lines.
Example requests. Your team asks in its own words.
What it can look up. What it won't do on its own.
It can look up
It won't do on its own
Doesn't Outlook already work with ChatGPT or Claude?
Many apps now offer their own built-in connection to AI assistants, listed in ChatGPT and Claude as apps or connectors. One person switches it on, signs in, and their assistant can reach that one app.
As of October 2026, all three big assistants work with Outlook. ChatGPT has Outlook email and calendar apps and can send from the chat since June 2026; on work accounts a Microsoft admin has to approve it. Claude's Microsoft 365 connector reads mail and calendar on work accounts and can send once an admin turns that on, while Claude's Outlook add-in, in beta, only drafts. Microsoft's own Copilot in Outlook drafts replies, and you select send.
So the question isn't which one can reach your inbox. It's what each draft is based on, who is allowed to send, and whether every person's assistant follows the same rules.
| Compared | Built-in connection | Set up for your team |
|---|---|---|
| Which assistant | ChatGPT, Claude or Copilot, each set up separately | The one your team already uses, set up once for everyone |
| Sending | Possible once an admin allows it | Drafts only. A person sends |
| What drafts are based on | Your mailbox | Your policies, orders, deals and tickets |
| Meeting prep | Your calendar | Your calendar joined with your CRM, books and help desk |
Checked in October 2026 on Microsoft's and the AI companies' own pages. These change often; we check yours on the free call.
The connection is the start. Your rules make it work for a team.
Your wording
Approved replies and SOPs, refreshed every night, so drafts use the current policy.
Roles
You choose who gets each package. In Sales, reps see only their own customers. Everyone signs in as themselves.
Approvals
Drafts only, in every mailbox. Refunds and exceptions go to the person you name.
Microsoft admin steps
We walk whoever manages your Microsoft 365 through the approvals it needs.
Training
A session per team, on their own inbox and calendar.
Kept working
When Microsoft or your other apps change, we fix the setup.
Where Outlook fits. Most teams start with one package.
Setup typically takes 1–2 weeks per package, for a fixed price in writing, then monthly care, which every package needs: your servers maintained, security updates and fixes when your apps change. Nothing is built until you sign the plan.
Outlook and AI. Straight answers.
Can ChatGPT connect to Outlook?
Yes. As of October 2026, ChatGPT has Outlook email and calendar apps, and work accounts need a Microsoft admin to approve them. Claude connects through its Microsoft 365 connector. We set up whichever your team uses, with your rules and a person sending every email.
Should we use Copilot instead, since we're on Microsoft 365?
Copilot works inside Microsoft's own apps. If your answers also need your CRM, books or store, what matters is how it's set up, not just which assistant. We help you choose on the free call, and we work with ChatGPT, Claude, Copilot and Gemini.
Does it work with a shared support mailbox?
Yes. Our shared inbox add-on works straight from the support mailbox your team shares, and replies stay drafts until a person sends them.
See it work with your Outlook. Book a free call.
Outlook is a trademark of Microsoft Corporation. ChatGPT and Claude are trademarks of OpenAI and Anthropic. Figure Hawk is not affiliated with any of them.