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<p dir="auto">Hi Mailmate Gurus,</p>
<p dir="auto">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:</p>
<pre style="margin-left: 15px; margin-right: 15px; padding: 5px; background-color: #F7F7F7; border-radius: 5px 5px 5px 5px; overflow-x: auto; max-width: 90vw;"><code style="margin: 0 0; border-radius: 3px; background-color: #F7F7F7; padding: 0px;">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@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
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<p dir="auto">Is there some setting I need to change to allow me to send outgoing mail?</p>
<p dir="auto">Thank you!</p>
<p dir="auto">Sincerely,<br>
Jonah</p>
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