Microsoft 365 and Outlook with Claude and ChatGPT: which connector for which mailbox

If your mailbox is a work or school Microsoft 365 account, start with Claude's official Microsoft 365 connector. If it is a personal Outlook.com, Hotmail, Live or MSN address, or you want it in the same search as your Gmail and iCloud mailboxes, that is what Fezola is for. Facts below were checked between 11 and 15 November 2026 and change fast.

Which connector for which mailbox

Claude's Microsoft 365 connector

According to Anthropic's help article (checked 11 November 2026), the connector is available on all Claude plans and is set up for work and school accounts: a Microsoft Entra Global Administrator must grant a one-time consent, and on Team and Enterprise plans an organization owner enables it. By default it reads and searches Outlook mail; sending, forwarding and drafting are optional write tools that the organization has to turn on, and they do not support attachments.

Fezola for personal Outlook mailboxes

Fezola connects Outlook.com, Hotmail, Live and MSN addresses through Microsoft's Graph API, with Sign in with Microsoft. It asks for the right to read, organize and write drafts, and to send only if you turn sending on. The sign-in is registered for personal accounts only, so work and school Microsoft 365 mailboxes are not supported yet; if you need them, tell us at hello@fezola.com. Step by step: Outlook.com and Hotmail in Claude and ChatGPT, or the short Outlook connector page.

ChatGPT

ChatGPT has a native Outlook connector. According to OpenAI's help page (read on 15 November 2026), it offers Outlook Email and Outlook Calendar apps for supported Microsoft accounts, including work and school accounts: searching and reading messages, finding people and contacts, shared or delegated mailboxes, with actions depending on Microsoft Entra consent and on what the workspace administrator enables. The page does not say which ChatGPT plans have them, so check yours. What Fezola adds is several providers in one search, Outlook.com next to Gmail and iCloud; as a custom connector it needs Business, Enterprise or Edu, with Pro read-only: see add an MCP server to ChatGPT.

Several mailboxes at once

Fezola is free for 2 sources; Pro is unlimited for $9 a month or $90 a year, with a 7-day free trial. One connector covers Gmail, iCloud, any IMAP mailbox and Outlook.com in the same search, with a shared Memory. See Claude or ChatGPT for email for how each assistant connects.

Create your free Fezola account to connect your Outlook.com or Hotmail mailbox.