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.

Thanks!

Nick