Connect Outlook to Claude and ChatGPT
Yes — Claude and ChatGPT can both read, search and reply to your Outlook through Mailopoly, which is listed in the Claude Connectors Directory and is an approved app in the ChatGPT app directory. Connect Outlook to Mailopoly by signing in with Microsoft, add Mailopoly in Claude or ChatGPT, and ask. The whole setup takes about a minute. Personal accounts (Outlook.com, Hotmail, Live, MSN) and work or school accounts both connect the same way, with a Microsoft sign-in rather than a password.
This guide also covers Hotmail, Live.com, MSN, Outlook.de / .fr and other country domains and Microsoft 365 work and school accounts — the steps are the same.
Before you start
- A Mailopoly account — 7-day free trial, no credit card.
- Personal accounts (Outlook.com, Hotmail, Live, MSN) and work or school accounts both connect the same way, with a Microsoft sign-in rather than a password.
- Claude on any plan, including Free, or ChatGPT with apps enabled.
Connect Outlook to Claude or ChatGPT in three steps
1Connect Outlook to Mailopoly
- Start a Mailopoly account at mailopoly.com/sign-up — 7-day free trial, no credit card.
- Choose Sign in with Microsoft and pick the Outlook, Hotmail, Live or Microsoft 365 account you want to connect.
- Grant the mail permissions Microsoft asks for.
- Mailopoly starts syncing straight away. Cleanbox sorts the inbox as it arrives, so your assistant sees it organised from the first question.
2Add Mailopoly to Claude or ChatGPT
This part is the same whatever you connected in step 1. Mailopoly is listed in both directories, so it's a search and a tap — no endpoint URL to paste.
Claude
- Open Settings → Connectors on claude.ai or in the Claude app — or choose Add connectors from the + menu in any chat.
- Search the directory for Mailopoly and choose Connect.
- Sign in with your Mailopoly account when prompted, then choose what Claude is allowed to do. Reading, making changes and sending are separate permissions.
- Back in the chat, make sure the Mailopoly connector is switched on, then ask.
One listing covers Claude.ai, Claude Desktop, Claude mobile, Claude Code and Cowork, and it works on every Claude plan, including Free. In Claude Code you can also run claude mcp add --transport http mailopoly https://fastapi.prod.aws.mailopoly.com/mcp-server/ and then /mcp to sign in.
ChatGPT
- Open the Apps directory in ChatGPT — from the + menu in any chat, or Settings → Apps & Connectors.
- Search for Mailopoly and choose Connect.
- Sign in with your Mailopoly account when prompted, then choose what ChatGPT is allowed to do. Reading, making changes and sending are separate permissions.
- In any chat, type
@Mailopolyand ask.
Mailopoly is an approved app in the ChatGPT app directory, so there's no developer mode and no endpoint URL to paste. Once connected it's available in every ChatGPT conversation on the web and in the mobile apps.
Using something else? Claude Code, Cowork, Codex and any client that supports remote MCP servers connect the same way — the Mailopoly MCP page has the endpoint and per-client steps.
3Ask about your Outlook
Whatever you've connected to Mailopoly is what your assistant can reach. Some things people ask on day one:
- Summarise what came into my Outlook Cleanbox today.
- Find the meeting invite from Priya in my Hotmail and add it to My Day.
- Draft a reply to the last email from HR from my work Outlook address.
What Claude and ChatGPT can do with Outlook through Mailopoly
- Search Outlook — and every other account you own — in one question. By sender, date, topic, or the half-remembered phrase somewhere in the body.
- Read your Cleanbox, not your whole inbox. Mailopoly sorts Outlook as it arrives: personal and important mail in Cleanbox, promotions and newsletters in Other. Ask for either.
- Summarise a thread, a day or a week. "What did the school send this week?" comes back as an answer, not a list of links.
- Reply from your Outlook address, in your voice. Save a draft to Mailopoly for review, or send — sending is a separate permission and a confirm-first action.
- Schedule a send for later, and cancel it if you change your mind.
- Pull out invoices, events and deliveries. Amounts and due dates, calendar invitations, parcel tracking — extracted on arrival and added to My Day.
- Find an attachment. Every attachment from Outlook lands in PolyBox, so "find the PDF the accountant sent" just works.
- Unsubscribe, snooze, file and mark read from the chat, on whichever account the mail belongs to.
Reading, making changes and sending are separate permissions you grant when you connect, and you can revoke an assistant at any time from Settings → Security in the Mailopoly app. More on the security page.
What goes wrong with Outlook, and the fix
- Claude's Microsoft 365 connector doesn't accept personal accounts. It needs a work or school account on a Microsoft business tenant, so Outlook.com, Hotmail and Live addresses can't use it. Mailopoly connects all of them.
- Work or school accounts: if your tenant requires admin consent for third-party apps, your IT admin needs to approve Mailopoly before the sign-in completes.
- More than one Microsoft account: connect each one separately — Mailopoly searches them together, and your assistant can reply from whichever address the thread belongs to.
7-day free trial, no credit card. Connect Outlook in about a minute.
Frequently asked questions
Other connect guides
Email providers
- Gmail
- Outlook
- Yahoo Mail
- iCloud Mail
- AOL Mail
- Comcast Email
- Zoho Mail
- Yandex Mail
- GMX
- Fastmail
- Any IMAP Mailbox
