[MlMt] Outlook requiring a new approval every day for the past few months (Sanchit)

[54.naps.model at icloud.com]

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, mailmate-request at lists.freron.com wrote:
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> Today's Topics:
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>   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 <ai.sanchit.123 at gmail.com>
> 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: mailmate at lists.freron.com
> 
> 
> 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 <http://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" <daveoran at orandom.net>
> Subject: Re: [MlMt] Weird problem with Spamsieve
> Date: July 11, 2026 at 7:46:53 AM EDT
> To: MailMate Users <mailmate at lists.freron.com>
> 
> 
> 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
>>>>> 
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>>> DaveO
>> 
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> DaveO
> 
> 
> 
> From: Robert Brenstein <mailmate at learning-insights.eu>
> Subject: Re: [MlMt] Weird problem with Spamsieve
> Date: July 11, 2026 at 8:40:28 AM EDT
> To: MailMate Users <mailmate at lists.freron.com>
> 
> 
> 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.
> 
> 
> 
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