Hello everyone, first post here.
I've started at a company where there was almost an entire turnover of the IT department. The last crew really had no idea what they were doing and guessed at most configurations by trial and error until it started working. With that in mind, here is the issue.
We are running Windows 2012 R2 on a physical standalone box hosting only Exchange 2013. This server has never had a single windows update performed on it since the day it came online many years ago. Over the past weekend we applied all of the windows updates through multiple rounds of reboots and got everything up to snuff. Unfortunately this has cause an issue with the OWA portion of exchange.
Users can send and receive through Outlook internal and externally. Users setup with exchange mail on their cellphones can send and receive email. When users go to https://owa.mycompany.com
they are greeted with a 440 Login Timeout error.
I have done a multitude of searching on the web and almost every 'solution' pertains to Exchange 2007 or 2010. None of them are for 2013 (although that hasn't stopped me from gleaning the information and trying fixes where appropriate) I've checked and reinstalled the SSL Cert on the webmail site, recreated the sites, checked permissions on the sites, etc. We're kind of at a loss with what the issue is at this point. The most I can offer is that Windows Updates 'broke' the site and seeing as we had over 1GB of updates it's somewhat hard to pin-point what might be the offending update.
Nothing on this server has been setup or configured with best practices adding to the confusion. Has anyone seen anything like this before?