[MlMt] Exchange Error - "server does not support any authentication methods"

H. Jonah Lefkoff jonah.lefkoff at gmail.com
Mon Nov 17 11:04:19 EST 2025


Hi Mailmate Gurus,

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 Ready to run action (type: 0, retry count: 3)
15:51:42 Clearing connection to smtp-mail.outlook.com
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]
15:51:42 C: EHLO [100.98.25.35]
15:51:42 S: 250-BL1PR13CA0181.outlook.office365.com Hello 
[155.33.135.35]
15:51:42 S: 250-SIZE 157286400
15:51:42 S: 250-PIPELINING
15:51:42 S: 250-DSN
15:51:42 S: 250-ENHANCEDSTATUSCODES
15:51:42 S: 250-STARTTLS
15:51:42 S: 250-8BITMIME
15:51:42 S: 250-BINARYMIME
15:51:42 S: 250-CHUNKING
15:51:42 S: 250 SMTPUTF8
15:51:42 Error: Cannot authenticate as “jonah_lefkoff at hotmail.com” 
since the server does not support any authentication methods.
15:51:42 Error code: 6
15:51:42 Failed action (0). Reset observed read/write timeouts: 8/8

15:51:42 Handling reply
15:52:13 Handling request
15:52:13 C: QUIT
15:52:13 S: 221 2.0.0 Service closing transmission channel
15:52:13 Clearing connection to smtp-mail.outlook.com
15:52:13 Ready to run action (type: 3, retry count: 0)
15:52:13 Clearing connection to smtp-mail.outlook.com
15:52:13 Completed action (3). Observed read/write timeouts: 8/8
```

Is there some setting I need to change to allow me to send outgoing 
mail?

Thank you!

Sincerely,
Jonah
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