I'm on a personal MSA (Outlook/Hotmail) which is giving these errors. Seems that MS was throwing the "authenticated but not connected" error as far back as 2023 - https://support.mozilla.org/si/questions/1416664.
On Sun, Jul 12, 2026 at 12:03 AM Henry Seiden <[email protected]> wrote: > I think my Outlook.com account is using one of those situations (it’s an > Office365 account) and OAUTH2 setting in MM, on both SMTP and IMAP client > side. Don’t know what the server config is but I’m not messing with success. > Respectfully, > Henry Seiden > E: Techworks Pro E-mail <[email protected]> > W: Techworks Pro Co. Home Page <https://techworkspro.com> > ------------------------------ > > Techworks Pro Co. > > Founder, Henry Seiden [email protected] > © 2025 techworkspro.com > > > On 11 Jul 2026, at 14:13, Maxim Guzman via mailmate wrote: > > Same here, and I think this is bigger than MailMate. > > I'm on a personal Outlook.com/Hotmail account (M3 Mac), OAuth2, same > outlook.office365.com endpoints for IMAP and SMTP. Identical pattern to > yours: the "authenticated but not connected" error, XOAUTH2 failing on a > token that should be valid, then MailMate deleting the refresh token from > the keychain so I'm forced to re-approve. Relaunch fixes it for a day, then > it repeats. > > The root cause looks server-side at Microsoft, not MailMate. There's a > documented regression in Microsoft's IMAP OAuth service for consumer > Outlook.com accounts, running since around December 2024 and still open. > After a good OAuth flow the XOAUTH2 handshake gets rejected with exactly > that "User is authenticated but not connected" string despite a valid > token, and it's hitting multiple independent mail clients, so it isn't > app-specific. Microsoft Q&A thread if you want to add your case: > > https://learn.microsoft.com/en-us/answers/questions/5673167/imap-oauth-regression-user-is-authenticated-but-no > > One caveat: that error string means different things by account type. On > consumer MSA accounts it's the regression above. On work/school (Entra) > accounts it usually means IMAP is disabled for the mailbox, or the app's > delegated permissions / admin consent are misconfigured, which is a tenant > fix rather than a Microsoft bug. Which kind is your account? If it's a > work/school tenant, the diagnosis and fix are completely different. > > Where I do think MailMate is at fault: deleting a perfectly good refresh > token on this failure. A transient server-side rejection shouldn't trigger > credential deletion. If MailMate treated "not connected" as > retry-with-backoff instead of purge-and-re-auth, the daily prompt would > mostly disappear even while Microsoft stays broken. Might be worth a look, > Benny. > > The durable fix is probably Microsoft Graph instead of IMAP for consumer > MS accounts. At least one client (MailVault) already abandoned IMAP OAuth > and moved to Graph for exactly this reason. Big lift for MailMate, I know. > Until then it's live with the daily re-auth or move the account to a > transport that doesn't use IMAP for Outlook. > > Best, > Maxim > > On Jul 11, 2026, at 12:00 PM, [email protected] wrote: > > Send mailmate mailing list submissions to > [email protected] > > To subscribe or unsubscribe via the World Wide Web, visit > https://lists.freron.com/listinfo/mailmate > or, via email, send a message with subject or body 'help' to > [email protected] > > You can reach the person managing the list at > [email protected] > > When replying, please edit your Subject line so it is more specific > than "Re: Contents of mailmate digest..." > Today's Topics: > > 1. Outlook requiring a new approval every day for the past few > months (Sanchit) > 2. Re: Weird problem with Spamsieve (David R. Oran) > 3. Re: Weird problem with Spamsieve (Robert Brenstein) > > *From:* Sanchit <[email protected]> > *Subject:* *[MlMt] Outlook requiring a new approval every day for the > past few months* > *Date:* July 10, 2026 at 1:03:19 PM EDT > *To:* [email protected] > > > I'm facing this issue on 6065 and it persisted when I upgraded to 6292, on > a M1 MacBook Pro with Tahoe 26.5.2. For the past few months, my Outlook > account pops up a prompt to approve MailMate's access every day. I'm using > OAuth2 with outlook.office365.com as both IMAP and SMTP server, and > almost all the time, the issue doesn't resolve by approving access on the > web page, it keeps popping up the page again & again after each approval > till it stops. After relaunching MailMate, approval works again and I only > have to approve it once. But the cycle repeats every day. I captured the > logs for one full cycle and in the non-working state (before the relaunch), > there are 3 command streams in the log, I've uploaded all 3 with some > redactions below. It starts with the error "D3 NO User is authenticated > but not connected.”. Command attempted: “D3 AUTHENTICATE XOAUTH2 > ••••••••••" and ends in the perfectly good refresh tokens (and the access > token and expiry date) being deleted from the keychain. Has anyone faced > this ? > > Logs: > > https://drive.google.com/drive/folders/1qkr5aMqjP0XjuY_jmxcADFYk3o726WE4?usp=sharing > > > > *From:* "David R. Oran" <[email protected]> > *Subject:* *Re: [MlMt] Weird problem with Spamsieve* > *Date:* July 11, 2026 at 7:46:53 AM EDT > *To:* MailMate Users <[email protected]> > > > On 9 Jul 2026, at 12:55, Robert Brenstein wrote: > > Check out the old threads for other suggestions. My main symptom was > beachballing when any action required spamsieve, that is new mails or when > I set an email as spam. Beachballing by new mails was easy to see since > spamsieve icons was getting red down arrow on the dock. An escape suggested > by someone was to switch to spamsieve rather than wait for timeout. Ah, > memory recall got triggered: my underlaying problem was some disk > corruption as it turned out. After I booted into safe mode and ran > diskcheck, which reported fixing something, the settings for full disk > access started sticking and the problem went away. > > Thanks, but no joy. I ran first aid from recovery, it found a few warnings > but no real problems. After reboot I turned full disk access off and on for > both Mailmate and Spamsieve. No change. Still beachballs. > > On 9 Jul 2026, at 15:39, David R. Oran wrote: > > On 9 Jul 2026, at 8:45, Robert Brenstein wrote: > > There were exchanges on such issues on this mailing list not long ago. For > me, the solution was to give full disk access to both mailmate and > spamsieve. Some of these settings did not want to stick, but once they did, > the problem went away. > > Thanks. Yeah I tried that back then to no effect. I just tried again > (turning it off and bak on again) and Mailmate still behaves as before. it > doesn’t beachball *every* time. but certainly 75% of the time or more. > > Robert > > On 9 Jul 2026, at 14:25, David R. Oran wrote: > > I don’t want to bother Benny with this, as I suspect I may be the only one > having this problem and it likely isn’t due directly to anything in > Mailmate itself. Perhaps somebody on the list might have clue. It’s been > happening for a couple of months now, but I can’t seem to relate when it > started to anything in particular. > > Here’s the problem. > - I have Spamsieve enabled on incoming mail in my set of InBoxes. > - Spamsieve is running. > - New mail shows up on the IMAP connection to my mail account. Mailmate > beachballs for anywhere from 20 seconds to a minute or so. It seems stuck > waiting on Spamsieve. > - If I click on Spamsieve explicitly, the spam check finishes immediately > and Mailmate becomes responsive. > > Most of my Spam is caught first by Spamassasin on my mail server, so the > majority is in the Junk folder already and doesn’t have a Spamsieve score. > However. > > - If I go into the Junk folder, select one or more messages, and > explicitly invoke Spamsieve to score them, the beachball happens just as > with new incoming mail. > > Something is happening with inter-process communication here, but I can’t > figure out what, or where to look in my Mac’s settings for clue. > > Possibly relevant: if for yucks I launch Apple mail which also has > Spamsieve set up, and mail comes in, Apple mail doesn’t beachball > communicating with Spamsieve. > > Clue bat? > > > DaveO > > _______________________________________________ > mailmate mailing list > Unsubscribe: https://lists.freron.com/listinfo/mailmate > > > _______________________________________________ > mailmate mailing list > Unsubscribe: https://lists.freron.com/listinfo/mailmate > > > DaveO > > > _______________________________________________ > mailmate mailing list > Unsubscribe: https://lists.freron.com/listinfo/mailmate > > > _______________________________________________ > mailmate mailing list > Unsubscribe: https://lists.freron.com/listinfo/mailmate > > > DaveO > > > > *From:* Robert Brenstein <[email protected]> > *Subject:* *Re: [MlMt] Weird problem with Spamsieve* > *Date:* July 11, 2026 at 8:40:28 AM EDT > *To:* MailMate Users <[email protected]> > > > You can contact Michael Tsai about this. > > On 11 Jul 2026, at 13:46, David R. Oran wrote: > > On 9 Jul 2026, at 12:55, Robert Brenstein wrote: > > Check out the old threads for other suggestions. My main symptom was > beachballing when any action required spamsieve, that is new mails or when > I set an email as spam. Beachballing by new mails was easy to see since > spamsieve icons was getting red down arrow on the dock. An escape suggested > by someone was to switch to spamsieve rather than wait for timeout. Ah, > memory recall got triggered: my underlaying problem was some disk > corruption as it turned out. After I booted into safe mode and ran > diskcheck, which reported fixing something, the settings for full disk > access started sticking and the problem went away. > > Thanks, but no joy. I ran first aid from recovery, it found a few warnings > but no real problems. After reboot I turned full disk access off and on for > both Mailmate and Spamsieve. No change. Still beachballs. > > > > _______________________________________________ > mailmate mailing list > Unsubscribe: https://lists.freron.com/listinfo/mailmate > > > _______________________________________________ > mailmate mailing list > Unsubscribe: https://lists.freron.com/listinfo/mailmate > > _______________________________________________ > mailmate mailing list > Unsubscribe: https://lists.freron.com/listinfo/mailmate >
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