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I’m using New Outlook. The first time I used it, it required me to create an app-specific password to access emails in my iCloud account. After I was able to access my emails, I turned off my computer. When I went back next time to access my emails, it told me again that I needed to create an app-specific password, which I did. After using it that way for a while, now it’s asking me a third time to create an app-specific password. Why is it not retaining the app-specific password?
Using Classic Outlook on Windows for personal email, calendar, and contact management
Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.
I have this issue periodically. This seems to be an issue. This is occuring and ongoing with icloud run through outlook!
I think the problem is unsuccessful logins. I got a lot of unsuccessful hacking logins. When that happens, it seems Outlook will disable the app password. Creating a new app password fixes the problem, until more failed logins come in and disable the new app password. Very annoying. Microsoft needs to provide a solution: sending alerts on unsuccessful logins and give owners an option not to disable the app password (when owner decides the app password is still good.) Plus, make the app password much harder (currently only 16 lower case letters.)
None of the above suggestions work. Every time I restart computer New Oulook asks for a new app-specific password for Apple email. No issues with Google mail.
None of these suggestions work because they’re generic AI responses.
I’m having the same issue as you and I refuse to believe Microsoft don't know about it.
Still the same issue. New Outlook always asks for app-specific password and act like a fresh installed copy after closing the app. If I Open another window while having the one opened, it works. After closing all of them, it acts again like a fresh copy. Anyway, it keeps the other (MS Exchange) email account with no problems. Forcing to change from Mail & Calendar app to the "New" Office is a travesty.
I am having a similar issue pulling emails from my hotmail account over to my gmail inbox. A few months ago the POP3 connection stopped working and getting a new app password fixed it. In the past month it has progressed from failing every few days, to now failing every few hours.
Alarmed to see that Microsoft support appear to be completely ignoring this issue.