1. BBGary's Avatar
    I am on iOS 16.2 public beta and started to receive those strange error messages regarding certificates from hotmail or outlook not being trusted by iOS.
    Anyone faced with those pesky error messages and if yes what was the way to fix the problem. I am trying to find a way that does not require reinstalling OS.

    Thanks a lot for every feedback
    11-07-2022 01:32 AM
  2. Up_And_Away's Avatar
    Not a beta tester but I can provide this possibility:

    If you’re seeing this for only certain websites/apps, the common thread may be they all are using the same certificate authority/CA (GoDaddy or whichever). If so then The new OS, for some reason, didn’t include the CA’s root certificate, didn’t add the intermediate, or for some odd reason the root-intermediate they did include wasn’t put together correctly (something as simple as a space within the file). Maybe they included the wrong CA root file altogether.
    https://support.apple.com/en-us/HT213464

    If you browse to hotmail and see the issue, click on the lock icon in the URL bar. You may then need to click more info. But it may give you a better reason such as the CA isn’t trusted. BOL
    BBGary likes this.
    11-07-2022 03:44 AM
  3. Ed7789's Avatar
    I am on iOS 16.2 public beta and started to receive those strange error messages regarding certificates from hotmail or outlook not being trusted by iOS.
    Anyone faced with those pesky error messages and if yes what was the way to fix the problem. I am trying to find a way that does not require reinstalling OS.

    Thanks a lot for every feedback
    I have seen them appear for my academic account over the past couple of days, and that’s on iOS/iPadOS 16.1.

    I don’t recall with precision what the error was, so I’m not going to be much of a help here

    I will update on my findings if it reoccurs.
    BBGary and Annie_M like this.
    11-07-2022 07:15 AM
  4. BBGary's Avatar
    Not a beta tester but I can provide this possibility:

    If you’re seeing this for only certain websites/apps, the common thread may be they all are using the same certificate authority/CA (GoDaddy or whichever). If so then The new OS, for some reason, didn’t include the CA’s root certificate, didn’t add the intermediate, or for some odd reason the root-intermediate they did include wasn’t put together correctly (something as simple as a space within the file). Maybe they included the wrong CA root file altogether.
    https://support.apple.com/en-us/HT213464

    If you browse to hotmail and see the issue, click on the lock icon in the URL bar. You may then need to click more info. But it may give you a better reason such as the CA isn’t trusted. BOL
    I use outlook.com email in a stock email app. My wife’s iPhone OS is 16.1 and still with the same issue
    11-07-2022 09:36 AM
  5. Annie_M's Avatar
    That's definitely curious. I rarely use Outlook, but I remember having issues when accessing Hotmail through the stock mail app. So, I switched to the Outlook App and haven't had any problems since doing so.

    One thing you might try is to remove Outlook/Hotmail from the stock mail app completely. Then, reboot your phone. Once your phone has rebooted, try adding it back to the stock mail app.
    BBGary likes this.
    11-07-2022 11:11 AM
  6. BBGary's Avatar
    That's definitely curious. I rarely use Outlook, but I remember having issues when accessing Hotmail through the stock mail app. So, I switched to the Outlook App and haven't had any problems since doing so.

    One thing you might try is to remove Outlook/Hotmail from the stock mail app completely. Then, reboot your phone. Once your phone has rebooted, try adding it back to the stock mail app.
    That did not work. Even removed the Microsoft Authenticator app.
    11-07-2022 12:37 PM
  7. Ed7789's Avatar
    That did not work. Even removed the Microsoft Authenticator app.
    Do you have a screenshot of the error message?

    I can’t seem to reproduce it today
    11-07-2022 08:40 PM
  8. BBGary's Avatar
    Do you have a screenshot of the error message?

    I can’t seem to reproduce it today
    I’ll try to add it
    11-07-2022 08:43 PM
  9. Up_And_Away's Avatar
    I use outlook.com email in a stock email app. My wife’s iPhone OS is 16.1 and still with the same issue
    Apologies, I thought this was an issue with the Beta 16.2.

    Specific to outlook, I’d second Annie’s advice, try the app. I successfully use outlook app and the stock Apple email app on my iPhone 16.1.

    Certificate authentication process definitely has some complexity. Besides the multiple elements of the chain of trust, there’s also cert type(Apache/Tomcat) and encryption/cipher levels and….trying to remember …client/server and CN/San potentials. How deep on the troubleshooting do you want to go?
    My layer 1 troubleshooting, after a reboot, is as Ed7789 suggests. Get the precise error. I usually paste in it a web search and see what it comes up with. Logs can be best of help but they’d likely have to come from server side (iphone logs I’m unaware of).
    I haven’t used Wireshark for checking cert authentication traffic but I’ve been told it can be done. I think there is a Wireshark for iOS (??) or other network analyzer options. But is getting very deep in troubleshooting. BOL
    11-08-2022 02:55 AM

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