Prompting for password on iPhone and only some Outlook clients after Windows Updates applied

Good evening -

So tonight after we applied updates to both exchange servers, we rebooted these servers and they both came back up.  I ran into an issue where I couldn’t reconnect back to Exchange through Outlook because it was prompting me for a password.  I waited a little while, and tried it again, same thing happened only this time after I clicked “cancel” on the password screen, it gave me the familiar 3 certificate errors, which is expected.  Eventually this kind of “went away”, but I rebooted the server a second time, just for good measure.  During this timeframe I checked with two people within the office to see if their Outlooks were effected and they were not.

Upon checking iPhone connectivity, I discovered I was unable to reach the mail server.  It was just timing out and telling me it could not be reached.  I had the other network guy try it on his iPhone and he said that he was prompted with a password dialogue box, which he clicked cancel on, and was then able to get to his mail just fine.  I also talked to our assistant, who resides on the second e-mail server and she said she is also being presented with a password dialogue box on her iPhone.  After I rebooted the server that second time, my iPhone was then able to connect, send, and receive e-mail, and it is currently still working.

Any help would be appreciated.


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pgetchellAuthor Commented:
I believe the issue resolved itself.
Shreedhar EtteCommented:

Does the Problem still exists? AS per your comment is got resolved after the second reboot.

If exists, there are any errors in the Application Event log of the server.

What is the version of the Exchange?

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