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

[Bill Cole]

On 2025-11-17 at 11:04:19 UTC-0500 (Mon, 17 Nov 2025 11:04:19 -0500)
H. Jonah Lefkoff <mailmate at lists.freron.com>
is rumored to have said:

> 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?

Enable "Require SSL" in the sending configuration.

The reason this failed is that when you connected to 
smtp-mail.outlook.com, it was an initially unencrypted connection 
(normal for port 587) which needs to have encryption initiated (using 
the STARTTLS command, but you don't need to know that) before it will 
allow authentication, which is perfectly normal because you don't want 
to be sending your password over an unencrypted session.

You may also need to enable OAUTH in this case, as it is a Microsoft 
service. I'm not sure if they are requiring OAUTH everywhere yet, but it 
is likely to be coming soon and should be possible for your account. 
That mechanism involves an out-of-band authentication through a web 
page, which passes back an authentication token to MailMate.



-- 
Bill Cole
bill at scconsult.com or billcole at apache.org
(AKA @grumpybozo and many *@billmail.scconsult.com addresses)
Not Currently Available For Hire