I've run into multiple problems trying to get "Old Outlook" to work with Modern Authentication. I know MA is in there, it tries, it just doesn't work. AOL, Hotmail, Gmail have all failed at points (and worked other times on other client PC's). Switching to New Outlook seems to work fine for Modern Authentication each time. It always returns with either a) Bad user/pass (but it is correct) or Server failure/no comms.
Has anybody else seen this? And yes.. Sometimes mail will work but not the calendar, or vice-versa (like a policy is on somewhere)... but these are end-user accounts.
If that ends up being the case for a client, I just let them know, "The New Outlook is where it's all going, like it or not, but your email is working!".
Seems like more planned failure/obsolescence, to me.
Reason: It's email. This is simple, established stuff. The code-base can't be that different between New and Old Outlook (In regards to MA) - and the MA features were added to "the old outlook", not that long ago. This has been going on for months, for various clients, for me.
So at the very least, MS is giving ZERO F's toward "The Old Outlook".
:reason
And yes, I've tap-danced Installing Office, uninstalling, cleaning reg keys, and waded into the abyss of asinine MS help articles and Reddit, Removed all accounts and mail accounts from Settings/Control Panel - Mostly to no avail.
I have not gone as far as full-reinstalling Windows and starting totally fresh for this particular issue - but I did do a repair install of 25H2 over-the-top... and the problem remains.
I have checked the email provider's settings, app-passwords, Security Settings, changed passwords and manually entered server settings, updates, BIOS firmware - none of that changes the problem.
A common thing seems to be that the user had 2016, 2019, 2021 or some version thereof - and then had M365 installed at some point.
Though again, fully removing ALL versions and doing various "cleanup ops" - then installing the latest... is still no go.
Anyways, it's far and few between, but I've already dealt with it 8-10 times.