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<p dir="auto">Hello Benny & Gregory,</p>
<p dir="auto">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?</p>
<p dir="auto">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.</p>
<p dir="auto">After reauthorization, things returned to normal on my Outlook account.</p>
<p dir="auto">HIH.</p>
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<div class="markdown" style="white-space: normal;"><p dir="auto"><br>
On 7 Mar 2025, at 3:40, Benny Kjær Nielsen wrote:</p>
<blockquote style="margin: 0 0 5px; padding-left: 5px; border-left: 2px solid #777777; color: #777777;">
<p dir="auto">On 6 Mar 2025, at 17:49, Dr Gregory Jefferis wrote:</p>
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<p dir="auto">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".</p>
<p dir="auto">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.</p>
</blockquote>
<p dir="auto">It should be using the same tokens as for IMAP. I don't think expiry is the problem.</p>
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<ul>
<li>Is there a way to force the OAuth dance?</li>
</ul>
</blockquote>
<p dir="auto">Yes, by deleting the related tokens in Keychain Access. They are named like this:</p>
<pre style="margin-left: 15px; margin-right: 15px; padding: 5px; background-color: #F7F7F7; border-radius: 5px 5px 5px 5px; overflow-x: auto; max-width: 90vw;"><code style="margin: 0 0; border-radius: 3px; background-color: #F7F7F7; padding: 0px;">com.freron.MailMate.Office365.oauth-*
</code></pre>
<p dir="auto">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.</p>
<blockquote style="margin: 0 0 5px; padding-left: 5px; border-left: 2px solid #777777; border-left-color: #999999; color: #999999;">
<p dir="auto">Or is a different diagnosis likely, perhaps mailmate no longer being an authorised app on the server end?</p>
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<p dir="auto">No, not if IMAP works, but SMTP can be explicitly enabled/disabled server side. I think <a href="https://learn.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission" style="color: #777777;">this</a> describes how to do this.</p>
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<p dir="auto">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:</p>
</blockquote>
<p dir="auto">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”.</p>
<p dir="auto">--<br>
Benny<br>
<a href="https://freron.com/support" style="color: #777777;">https://freron.com/support</a></p>
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<p dir="auto">mailmate mailing list<br>
Unsubscribe: <a href="https://lists.freron.com/listinfo/mailmate" style="color: #777777;">https://lists.freron.com/listinfo/mailmate</a></p>
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