Thanks Bill, Henry, and Benny for the advice.

The solution was to change the SMTP server address from `smtp-mail.outlook.com` (what was put in by default) to `outlook.office365.com` which then allowed me to check the OAuth option in the SMTP section. This resolved the sending issues.

Jonah

On 17 Nov 2025, at 15:04, Benny Kjær Nielsen wrote:

On 17 Nov 2025, at 17:04, H. Jonah Lefkoff wrote:

I’m running r6272 with three accounts, one of which is a @hotmail.com outlook account. I’m unable to send messages from this account, but can fetch and move existing messages between folders/trash just fine. Watching the activity viewer under the SMTP tab for this account while I press the “retry” button on the failed send, I get the following log:

```
15:51:42 Attempting to connect to smtp-mail.outlook.com:587 (Network.framework, plain text) 15:51:42 S: 220 BL1PR13CA0181.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 17 Nov 2025 15:51:30 +0000 [08DE251370C95BA9]
```

You can use `outlook.office365.com` (which is where it's connecting anyways according to the above). That should make MailMate display the OAuth2 option which you likely need to make this work.

(And use the same hostname for IMAP.)

--
Benny
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