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How can you prevent the MS Outlook IOS app from constantly signing out of my iCloud mail account?

How can you prevent the MS Outlook IOS app from constantly signing out of my iCloud account? It stays signed in for Gmail and MSN, but I have to continually re sign in to link my iCloud mail account. Happens on both the Outlook app for iPad IOS and IOS on my iPhone X. I prefer not to have to turn off two factor authentication on my iCloud account.

iPad Pro 10.5-inch, Wi-Fi, Cellular

Posted on Jan 18, 2020 3:21 PM

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Question marked as Top-ranking reply

Posted on Jan 23, 2020 9:46 PM

Thank you for the prompt response. Microsoft has been looking into it for a bit now but they say it’s an Apple issue. Apple thinks it’s a Microsoft issue. Hmmmm... In the meantime I think I found the cause and solution.


I found that the IOS Outlook apps would only seem to require re signing into my iCloud mail account after using / auto logging in from a different IOS or OS device (e.g use the Outlook app on my iPhone and then later using Outlook on my iPad). When that happens and your using two factor authentication with iCloud, you’re required to generate a new random app password from Apple to log back in every time. That workflow generates a new unique password every time to use for that particular device app, as it should be for security. But that appears to cause the problem here. When I cut and pasted the same initially generated password from the first attempt into the other IOS Outlook apps once they lost the log in connection (kept the same single generated password for my iPhone (IOS) and then also used that for my ipad(iPadOS) and then also my Macbook (Mac OS), the problem went away and I’m now staying logged in across all OS’s and device types. Unfortunately, that requires you to write down or copy that generated password someplace for later use if needed as that’s not stored in Keychain or is visible after you hit ‘done’ when generating app specific passwords. The key was to use only a single same app specific generated password across all your iOS / Mac OS devices and their various Outlook apps.

2 replies
Question marked as Top-ranking reply

Jan 23, 2020 9:46 PM in response to LACAllen

Thank you for the prompt response. Microsoft has been looking into it for a bit now but they say it’s an Apple issue. Apple thinks it’s a Microsoft issue. Hmmmm... In the meantime I think I found the cause and solution.


I found that the IOS Outlook apps would only seem to require re signing into my iCloud mail account after using / auto logging in from a different IOS or OS device (e.g use the Outlook app on my iPhone and then later using Outlook on my iPad). When that happens and your using two factor authentication with iCloud, you’re required to generate a new random app password from Apple to log back in every time. That workflow generates a new unique password every time to use for that particular device app, as it should be for security. But that appears to cause the problem here. When I cut and pasted the same initially generated password from the first attempt into the other IOS Outlook apps once they lost the log in connection (kept the same single generated password for my iPhone (IOS) and then also used that for my ipad(iPadOS) and then also my Macbook (Mac OS), the problem went away and I’m now staying logged in across all OS’s and device types. Unfortunately, that requires you to write down or copy that generated password someplace for later use if needed as that’s not stored in Keychain or is visible after you hit ‘done’ when generating app specific passwords. The key was to use only a single same app specific generated password across all your iOS / Mac OS devices and their various Outlook apps.

How can you prevent the MS Outlook IOS app from constantly signing out of my iCloud mail account?

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