Mail will not update after iOS 14.0.1 installation

Okay - so I just spoke to an apple adviser about this problem and they said they are aware of it. The adviser said in order to fix the issue I need to go to ‘settings’ - scroll down to ‘mail’ - click ‘mail’ - go to ‘accounts’ - click on the email address which is a problem - scroll down to ‘delete account’ - click to delete - then click ‘add account’ - choose email provider ie outlook etc - enter email address then password. Apparently this fixes the problem. I have three accounts which are constantly asking me to re-enter password, so I’ll do this for all of them and fingers crossed this annoying issue will be resolved. Fingers crossed.

I have the same problem. You have to look at the top of your screen. If it says ‘login.microsoftonline.com’ you have to cancel, because you will get the message to use your work email. When you click ‘re-enter password’ again and it says ‘login.live.com’ then you can enter your password. Sometimes it starts with ‘login.microsoftonline.com’ and after a few seconds it changes to ‘login.live.com’.

upgrade to iOS 14.2 which was recently released

You do not need outlook app for email on an iPhone.

Remove your email account and set it up again

On your computer, sign in to your email provider's website. Make sure that all of your email is there or make sure that your email is saved somewhere other than your iOSdevice. On your iOS device, go to Settings > Passwords & Accounts.

If you can't receive email on your iPhone, iPad, or iPod touch ...

My solution was to ditch the Apple productivity app and use the Microsoft Outlook app. Got my email functionality perfectly again.

Problem solved. It was actually in the companies end. They implemented DUO security. Installed it and now all’s good.

I think I may have a solution, not sure, just maybe.

I deleted my Outlook account and re-added it MANUALLY, that is adding it as “Other” in the iOS settings instead of as “Outlook”.

You have to enter the Outlook host name etc but it’s not too hard. My theory is that the password is retained in the manual settings differently.

(I also re-added the same account as “Outlook” as well so I had two of them, the “Outlook” one has failed after a day or so but the “Other” one hasn’t)

It might be a coincidence but worth a shot, I don’t think Apple is coming to our rescue here!

I updated to iOS 14.2 yesterday and have only had to renter my password once since the update. Hopefully that’s it fixed...

I believe this is a shared problem between Microsoft and Apple.

Microsoft’s issue is that their servers will periodically return an error, and immediately retrying will get continued errors.

Apple’s problem is once they get enough errors, it will no longer attempt to use the password. There is no button to say “retry the password I entered yesterday, it will work now”.

Now it is possible that the password is not stored on the phone and that only a validation token of some sort is on the phone. If this is the case, then it is probably all Microsoft’s problem, but I suspect the issue is shared. I have the same email accounts on phone and pad, and only one or the other “forgets”. If Microsoft was resetting credentials, I’d expect both devices to fail.

I'm running 14.2 as are many of my customers - still prompts the same every day.

I've tried the old delete email account and re-add "fix" now, let's see what happens tomorrow.

*I've noted there are some extra encryption settings which have appeared in the advanced section of the account (once the account is re-added) which I haven't noticed previously, so perhaps this is the actual cause? just a guess of course.

*Please also note, deleting your account will delete it's signature (assuming you have different one set per email account) so you will need to re-add back one ether account is re-added.

I think I will apply for a job with Apple now..

Same problem. This morning for the first time I get a request to verify my Outlook password. I’ve had the Outlook account for several years on six iPhone models without a problem.

Using the Outlook account in my Apple Mail app, it requests I verify my password. When I click the link to do so it gives me an error in the page below.

I get the same thing if I try to add a new Outlook account in iPhone Settings>Mail> Accounts>+>Outlook.

On my iPhone and MacBook I have had major issues with having to enter my outlook hotmail password everyday. Mail gets stuck in the outbox and mail is not received. I have spoken to Apple technical twice and we have deleted the account and reinstalled it but it had happened again today. My issue has been escalated but it must be an Apple issue because I have spoken to my daughter and her husband and they have been having the same issues. Apple is going to have to fix this issue.

I’m having the same problem. I updated to iOS 14.1 on Sunday and when I woke up on Monday I was asked to re-enter my password for an @hotmail account. Wasn’t straightforward and ultimately I had to go through the process to change my password etc before I could see my emails. Woke up this morning (Wednesday) and now I’m being asked to re-enter my password for a different email @hotmail. What’s going on Apple???

Should read:

Please also note, deleting your account will delete it's signature (assuming you have different one set per email account) so you will need to re-add back ONCE THE account is re-added.

Sorry, fat fingers here.

Im on 14.2 on an iPhone 8 (*as are most of my customers). Doesn't matter what you do, the account prompt problem still occurs daily.

Just to clarify:

1). Im using 2fa (with authentication app) with a hotmail.com account.

2). Both iOS 14.1 and 14.2 have the same prompting password daily issue. Deleting and removing the account doesn't work.

3). Unable to setup as exchange account (as kir424 suggested above) - just hangs on config screen so is setup using the outlook.com option when configured (as it has always been for a very long time) across many different iPhones and iOS versions.

Problem affects many people, all with iPhones / iPads (even some brand new iPads) have the same daily password prompt since upgrading to iOS 14.1 or 14.2. This is getting silly now.