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!
Clearly not, I'm on Windows 11 Pro with the same issue.
I have Windows and I bought Windows Pro prior to reading issues. It expired to download. Is it worth the change to W11 Pro? My 365 Family Office owner as well. Thanks. I have issues with Office 365 for 4 years and never hear from support. I opened a second family account and made my Outlook. com the primary and my aol.com a secondary account and created several outlook primary accounts for future.
Clearly not, I'm on Windows 11 Pro with the same issue.
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.
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