iPad 'Cannot verify server identity' error

As ridiculous as this sounds, the only real fix I have found to work is to delete the offending email account from your iPhone and the add it back. That seems to clear it.

You need your username and password to add your account, so be sure you have it before you delete it!

When you are adding the account, there will be a list of accounts, including Gmail, AOL and Outlook.

Even if your email account is an @live.com email address, instead of @outlook.com, choose Outlook.com.

After 30 minutes the message had not shown up again.

If I am correct, the account settings are changed from an imap to pop3. It doesn't matter to me HOW I get my emails, as long as I get them securely!

Good luck!

In my case the problem was, that the new certificate was only issued for outlook.com but I had „imap-mail.outlook.com“ set as incoming mail server.

Go to Settings > Mail > Accounts

select your Microsoft email Account.

then check Account > Host Name

unter INCOMING MAIL SERVER

and change it to outlook.com and save the change.

I had an older live.com email account that I believe was the issue. I deleted the account and then added it again. I did notice that before deleting it had Notes selected for the account (along with mail, contacts, calendar, reminders) but when adding it back Notes was not an option at all. I have not had the pop-up errors anymore.

Go to Settings > Scroll down until you see > ( MAIL ) than ( Accounts )

Look for ( Hotmail ) - was my email - (Make sure you know your password before deleting) = Delete It

After it's deleted go back and at the bottom Add Account - (Email address & Password)

Solved my annoying message from returning. Hope this helps.

When I look at the cert in question, it references outlook.com instead of office365.com so I changed my smtp server settings in mail and outlook to outlook.com from outlook.office365.com and it resolves, passes mail, no cert issue. I imagine it would work for imap users who manually configured their servers. Change from imap server imap.office365.com to outlook.com. Looks like Apple maybe requiring a match now.

I just sought Apple help via “Apple Support” today, the guy studied my issue and suggested the following way:

General > Reset > Reset Network Settings

After reset, reboot your iPhone and send test email to yourself.

it seems working for me. Such prompt not reappear so far.

Looks like this worked. So far no error msg.

IPHONE 12 PRO IOS VER 14.1

STEPS:

GOTO: SETTINGS

GOTO: CONTACTS

GOTO: ACCOUNTS SELECT OUTLOOK FROM THE LIST <ENTER>

DELETE OUTLOOK ACCOUNT (AT THE BOTTOM) <ENTER>

GOTO: SELECT <BACK> SELECT ACCOUNTS <ENTER>

SELECT ADD ACCOUNT <ENTER>

SELECT OUTLOOK.COM <ENTER>

WHEN THE SCREEN COMES UP SIGN IN: YOUR MICROSOFT ACCOUNT NAME (MAIN ONE) <ENTER>, THEN YOUR

PASSWORD (MAIN ONE) <ENTER>

WHEN NEXT SCREEN COMES UP HIT <SAVE>, ACCOUNT ADDED AND IT RETURNS TO ACCOUNTS LIST. OUTLOOK SHOULD

BE THERE

LEAVE AND BACK TO MAIN HOME SCREEN.

GOOD LUCK! WORKED FOR ME ON A BRAND NEW IPHONE 12 PRO

I did manage to stop the pop up for now. In my case, the bug affected Gmail and Outlook and was unrelated to iOS updates, since my phone is on an older iOS. I also did not have a "trust" button that could fix the issue, like so many here. So, I deleted my accounts again (made sure I was also logged out of the accounts on their websites) and then re-added them manually, instead of using the Google or Outlook buttons at set up. The SSL toggles were able to be "on" using this method too, which was not the case when I used the suggested buttons to set up before. Don't know if it fixed the trust issues but it is at least a workaround that enables me to use my phone. I did not update my iOS. Only posting this in case it is a temporary fix for someone else. Good luck everyone!

Seems in my case I was able to get rid of this annoying and persistent message, at least for now, on both my iPad and iPhone without actually having to delete and re-establish the entire account. Apart from upgrading to 14.1 (which by all accounts isn’t the fix) all I did was under Settings -> Mail -> Accounts toggle the Mail button off and back on again for the offending account. I also accessed the Advanced Settings by clicking on the account email from that same screen and then toggled SSL off and on again while Mail was on. Hasn’t happened again on either device since I did that yesterday afternoon. Can’t say for sure which of these steps actually fixed it though. Good luck to all with fixing this, as it really gets in the way of using your device.

Ok so I think I figured this out. Was so frustrating. Go to your email information in settings. (Where you can change your password etc) setting-mail-accounts-then pick your email provider and continue on to where you can change your account info.

I found that my Host name was changed to imap-mail.outlook.com. So I changed it to what it’s supposed to be for my Hotmail. Which was smtp.live.com.

if you don’t know what your host name is supposed to be then just Google it. That’s how I found out my Hotmail host name. It stopped for now. Hope it stays that way. Good luck!!

I had the problem on my iPhone (starting 12/5/2020, using a Dreamhost-based server) and fixed it. Swiping out and rebooting did not help me. What did the trick was deleting the mail account on the iPhone and the re-creating it. It was a bit of a pain, but I managed the whole process in under 30 minutes, and now e-mail is back and the annoying popups are gone.

When you are setting up your hotmail account don’t use Outlook server but pick Other and than use your e-mail address and password (Microsoft may give you applications password instead of your regular password, use that one ). Once you do that you can delete your hotmail account that you setup as Outlook and use this new one. Problem solved but you may lose some contacts when you delete hotmail/outlook account