On 2025-11-17 at 11:04:19 UTC-0500 (Mon, 17 Nov 2025 11:04:19 -0500)
H. Jonah Lefkoff <[email protected]>
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 “[email protected]”
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
[email protected] or [email protected]
(AKA @grumpybozo and many *@billmail.scconsult.com addresses)
Not Currently Available For Hire
_______________________________________________
mailmate mailing list
Unsubscribe: https://lists.freron.com/listinfo/mailmate
