On 6 Mar 2025, at 17:49, Dr Gregory Jefferis wrote:
I use mailmate to with 3 email addresses. For one I rely on oauth2 to
connect to a Microsoft outlook SMTP server. As of the last few days
when I try to send a message I just see the message go to Drafts and
have state "Pending submission".
I wonder if the OAuth authentication may have expired. If so I would
have thought that Mailmate would automatically trigger OAuth dance,
but this doesn't seem to happen.
It should be using the same tokens as for IMAP. I don't think expiry is
the problem.
* Is there a way to force the OAuth dance?
Yes, by deleting the related tokens in Keychain Access. They are named
like this:
com.freron.MailMate.Office365.oauth-*
Note that Keychain Access has some weird old behavior/bugs where you
some times have to explicitly select the keychain to the left in order
to make deleting work.
Or is a different diagnosis likely, perhaps mailmate no longer being
an authorised app on the server end?
No, not if IMAP works, but SMTP can be explicitly enabled/disabled
server side. I think
[this](https://learn.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission)
describes how to do this.
I see no sign of activity in the SMTP tab of the activity viewer when
I send a message. There are 4 lines showing EHLO messages but no
obvious error state:
Ok, that does seem a bit strange. I would expect it to reject
authentication if it was disabled server side (but I don't know this for
sure). Maybe send me a screenshot of your IMAP account settings window
via “Help > Send Feedback”.
--
Benny
https://freron.com/support
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