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

[Henry Seiden]

Hi Jonah,

A couple of things to consider:
1. I am unfamiliar with any Outlook account that does not have outlook.com or office365.com after the @. Please explain with an example of how it is set up on MM. If you want, try send me a message directly to my address off list so I can see the above. I’d also like to see the error message if any, screenshot that you get in MM when attempting to send on that account. Does the same setup work with other email clients (like Mail.app)? Please indicate how you are sending and from which client in the email
2. The current beta of MailMate is 6090 and is the one I use for all my (10) accounts, one of which is @outlook.com. My settings which supposedly are in the new format for Microsoft email, shows OAUTH as being selected. I am told that previous versions of Outlook server settings would also work (pre-Live.com). Someone else can confirm this. My settings of SMTP (with OAUTH2work for me.
3. From your message I see the error you show as detected at Live.com and/or Outlook sever end are 250-PIPELINING and 250-Authentication of your actual send address. Is it “jonah_lefkoff at hotmail.com”? Is that also the actual address you have set up in MM? If not, have you tried simply using the Outlook address without Hotmail, then engaged OAUTH2 checkbox in the IMAP settings within MM, using the SMTP Server setting as smtp.office365.com?
4. Or, as shown in your error list, is it actually [jonah_lefkoff at outlook.com](mailto:jonah_lefkoff at outlook.com)? The parsing error would likely be attributable to this setting/configuration. You might try simplifying it.
5. Be advised that you can also reach out to Benny by reporting this on Feedback and including a MM error log place of the Activity Monitor listing. If you need help engaging the MM Error log, let me know.

My system: MailMate/6290/8E0C2B09-5E7C-51C0-A74E-30C066DF8C4A 26.1.0/arm64/Mac16,5/14

Respectfully,

Henry Seiden
- -
Techworks Pro Co.
E: info<at>techworkspro<dot>com
W: http://techworkspro.com

On 17 Nov 2025, at 11:04, H. Jonah Lefkoff wrote:

> 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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