My iPhone 12 keeps asking for email password

I found a temporary workaround for Hotmail (Outlook.com) issues to keep receiving push emails without retyping the PW over and over again: setup Hotmail as imap account, this seems (till now) not affected. Hopefully Apple resolves this annoying problem in the next update!

Receive:

imap server: imap-mail.outlook.com

use SSL: on

Authentication: password

port: 993

Send:

smtp-mail.outlook.com

use SSL: on

authentication: password

port: 587

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 have 3 Hotmail/Outlook accounts that I access via the Apple Mail app and was getting password requests for all 3 but different amount of times for each account. I spoke to their support and deleted one account from my phone, rebooted my phone then I added it again. Since that I have not had a request for that account when they were coming quite regularly, it has now been 3/4 days since I did it and not a single request since.

Fingers crossed!

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!

No repeating password entries anymore: as temporary workaround I added my 3 hotmail accounts as IMAP accounts (mail only) and turned off push-mail in the original Outlook.com account settings. Apparently hotmail calendar and contacts aren’t affected. Disadvantage is that IMAP doesn’t support push, only fetch, so that mails don’t arrive immediately. But that’s better for now than logging into all my 3 accounts (with strong different passwords) over and over again.

Nevertheless, Microsoft and Apple must solve this! Unfortunately the developers seem not to check this forum...

I deleted the Mail app completely and re-installed it and I've been password pop up free for over a week now... it's been my fix on the XS Max. Try it!

I deleted Hotmail account then re added it using the ‘other’ category not the outlook button, not had to re enter since

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!

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.

There was a piece pop up on my news feed tonight. This is happening to a lot of people. The fix recommended and has so far worked for me. Sign out if ICloud ( go to setting click on banner and scroll down to sign out ) turn off the find my phone feature. Shut down and restart the phone. Sign back into iCloud. So far. Fingers crossed it’s worked.

So I went into Apple and they couldn’t fix an issue I was having with “cannot verify server identity” popping up several times a day. They couldn’t fix it and had to escalate it. I was called by Apple later at home. After a couple hours of troubleshooting they finally decided to restore the phone from backup. No more issues with anything so far including email. It’s been 2 days. Crossing fingers.

Outlook mail

I may have a solution... I deleted the Mail app and reinstalled two days ago and *touchwood* I’ve not had the password pop ups since!

I have had the same problem. Today i have deactivated „compromised passwords“ in settings and until now, i have had no more pop-ups to reenter my hotmail/live password(s).

The culprit that causes this issue for months is Circle. If you have it enabled, consider turn it off to see if it fixes your issue.