[MlMt] Forcing OAuth2 reauthorisation

[Benny Kjær Nielsen]

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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