[MlMt] Forcing OAuth2 reauthorisation

[Henry Seiden]

Hello Benny & Gregory,

FWIW, I have the new setup (WindowsLive) as one of my source accounts. My OAUTH settings in MM are now and have been OK. But as per recent actions, if there is a OS action like using a Beta version of MacOS or iOS WindowsLive gets pretty picky,  Sends me to reauthorize screen to update. Perhaps this is relevant to your issue?

My server accounts have been the same since M$ began using Windows Live for Outlook accounts, migrating completely to WindowsLive for Outlook. It was a ‘gradual’ transition. You didn’t mention if you use Outlook or Windows Mail though. I suppose that may be different.

After reauthorization, things returned to normal on my Outlook account.

HIH.

Respectfully,

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

On 7 Mar 2025, at 3:40, Benny Kjær Nielsen wrote:

> 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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