Using Classic Outlook on Windows for personal email, calendar, and contact management
This is still an issue as of mid-January 2024. I also have the exact issue you describe. It is extremely annoying!
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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
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This is still an issue as of mid-January 2024. I also have the exact issue you describe. It is extremely annoying!
None of these steps help - also, this response feels like it was written by AI.
Still an issue as of 18 Jan 2024
Its happening with me as well on hotmail. I havent uninstalled Outlook yet but have tried deleting and creating App passwords. Seems like they work for a while but it eventually gives me a popup.
Happening here as well, with both my Outlook and Hotmail accounts. Using Outlook 2013.
No issues with OWA logins.
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?
It is January 31, 2024 and I too have been experiencing this same issue. I have tried all of the trouble shooting suggestions to no avail. Microsoft, please review and correct.