My iPhone 12 keeps asking for email password

Since no one from apple has provided a helpful suggestion, I'll venture this one.

Unfortunately, some updates force apps to break just a little when they have to adjust some security settings.

What I have tried (just today) is:

1. 1. Go to Settings > Mail > Accounts
   2. your accoutns will be listed there.
   3. Tap one by one, and check for those that say in red letters "Re-enter password"
   4. Do not re-enter your password (as we have seen, this doesn work).
   5. Instead, go down to delete account, confirm "Delete from my iPhone"
   6. Then go back to accounts, and add the account back in by tapping "Add Account"
   7. Then when the password is asked, enter the password manually, do not use the iOS keychain saved passwords. (this could also be broke or corrupted in some way after the upgrade, better to be safe)
   8. When you enter the password manually, keychain will also update itself with whatever you just entered as a password.

I still do not have evidence that this actually works, but being in IT and security support for a while, leads me to think that is the best route to go... considering that apple may never even see or reply to these posts.

If you think this helps, please mark it as helpful and share your results with a reply so other may benefit from this, or flat out know that my suggestion does not work at all :P (please be constructive with your feedback)

I think I may have found a solution: go to the “Reminders” or “Calendar” app settings. Mail may work too but I do not use the default Mail app.

Then go to Accounts and finally select Outlook. You will probably have a prompt to sign back in to outlook, like I did. The problem seems to have resolved itself after doing this.

If you have not set up multi-factor authentication with Microsoft’s Authenticator App, now would be a very good time to do so to protect yourself!

I have same issue. I have over 10 email accounts from Hotmail, Gmail and my dedicated company outlook email addresses and every day I get same pop ups.

Worked fine on my old iPhone 7+ with ios14, but since moving to iPhone 12 Pro with IOS14.2 I have nothing but issues

I uninstalled and reinstalled my hotmail/outlook account and the problem disappeared. I've seen this appear as a solution and a lot of people seem to have success with it. I think this is an IOS 14 issue because I never had it before but coincidently, I upgraded to a new iPhone 12 at the same time I got the new IOS. Anyhow, this seems to have worked for me and for a lot of others. Here are the instructions:

1. Go into Settings > Mail.
2. Scroll down to Accounts > Outlook.
3. Select Delete Account.

Once the account is removed, you can add it back in using Settings > Mail > Accounts, and then select Outlook for the type of email account you want to add back in. If you have any trouble doing that, turn your phone off and back on between deleting and adding your outlook account back.

Good luck!

HI GUYS. I DID POST THIS ANSWER A FEW DAYS AGO BUT I'M NOT SURE IF IT POSTED. ANYWAY! HERE IT IS WITH PICTURES. IT WORKED FOR MY IPHONE 11 PRO AND SEEMS SO FLIPPING SIMPLE. GO TO SETTINGS, THEN SCROLL DOWN TO PASSWORDS. CLICK ON THE PASSWORDS TAB AND THEN CLICK THE AUTOFILLPASSWORDS TAB, IT WILL PROBABLY BE IN THE OFF POSITION. CLICK IT TO THE ON POSITION. HOPE IT WORKS FOR YOU, IT DID FOR ME. PLEASE SOMEONE LET ME KNOW. NOT SURE HOW ALL THIS COMMUNITY STUFF WORKS.

I have a iPhone 11 pro on IOS 14.2 and this same keep asking for Hotmail password has been going on for a while now! It also does the same on my iPad which has up to date IOS on it , very annoying as It dosent keep asking me on my PC, so surely it must be an IOS problem? Glad to know im not going mad as there are lots of us with the same problem!

I’m having the same issue since the iOS 14 update on my iPhone 8. Periodically prompted to re-enter my password for my Hotmail account. Really annoying. Is anyone from Apple taking note and doing anything about this?

This is not true... it IS absolutely an iOS issue. Happening to me also, using iP8, and only started after upgrading to iOS 14 (and have since updated twice more to the latest version of iOS 14, with still no resolution).

Oddly enough, it seems to affect one of my hotmail accounts more than the other (though I have had the issue with both of my Hotmail accounts, just at different frequency).

Never had this issue prior to iOS 14, nothing else has changed. And judging by the number of people complaining about it online (including on the MS forums, where again it's been confirmed it's an iOS issue, given it only happens in the default Mail app, and not other mail apps), I would hope that Apple is going to release a fix soon!

I used my phone to

• Read emails (doesn't work as per this thread)
• Listen to music (doesn't work)

It took all of about 2 days until I bought an Android phone. The experience on Android is pretty terrible, but I can listen to music and use email, which seems too complex of a functionality for Apple to support.

Apple introduced the following two features as part of iOS 14.x; these features potentially introduce issues on a personal network and with any services that uses hardware MAC addresses and/or authentication "timing".

Private Network Address

https://support.apple.com/en-ca/guide/iphone/iph6b324bb33/ios

https://support.apple.com/en-ca/HT202068

Check For Weak Passwords

https://support.apple.com/en-ca/guide/iphone/iphd5d8daf4f/ios

The simplest method of troubleshooting issues related to authentication and connectivity are:

• Disable Private Network Address
• Disable Detect Compromised Passwords

An additional step is required if the keychain is sync'ed to the Apple Cloud; the step involves forcing a refresh/sync. This is achieved by simply navigating to Settings > [iCloudAccountName] > iCloud ... the action of navigating the iCloud settings is enough to force a refresh. If you have multiple iOS devices devices connected to an account and sharing settings via the Apple Cloud; ensure to perform the steps at each device so as to ensure that the keychain is consistent.

One completed, close any running apps on your device.

Quit and reopen an app

https://support.apple.com/en-ca/guide/iphone/iph83bfec492/ios

This effectively restores pre-iOS 14 behaviour and simplifies troubleshooting.

I am having the same problem. New iPhone 12! I have 10 email accounts, not just with outlook, and the phone keeps asking me to input my passwords nearly everyday. It won’t store them. Really frustrating!

I have the exact same issue as the OP, and I concur this has nothing to do with the Hotmail server, rather than an iOS glitch/issue that needs to be resolved ASAP.

Just like the OP, I too have the outlook (Hotmail) app downloaded and it never requires me to re-enter the password each day as the Apple Mail does to all my Hotmail accounts. Screenshot attached for reference.

I’m having the same issue here, at least once a day. I followed all the helpful tips but the same issue keeps happening. I’m starting to loose my patience, if you have found a solution for this please share with us.

I agree, if I go onto the live.com and sign in to my emails there the pop up disappears, but it is not retaining the information and is only for the outlook email address, all other addresses are fine

I can assure you this is happening on my IPad and iPhone since updating to iOS 14 and only for my hotmail account. What I have noticed is the password for live.com is not storing in my passwords on iOS so definitely an iOS issue