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OWA issue - Exchange 2013 - 440 Login Timeout

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Last Modified: 2017-03-14
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?

Thanks
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SaberSupport Escalation Engineer
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Scott CSenior Engineer
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How about if they use OWA internally?  Does that work?
ChickpeaSystems Administrator

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Scott C, did a quick check in Programs and Features and Exchange is at CU13, also executed the command you provided and got a Version 15.0 (Build 1210.3) returned. Definitely going to update that immediately.

As for OWA internally, that does not work either. I cannot open up the Exchange Administration Center on the server as well.
ChickpeaSystems Administrator

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Saber, I will give that a look as well after I apply the update. As much as I wish the CU15 would fix the problem, I'm guessing it probably will not. At least I'll be up to date though!
SaberSupport Escalation Engineer
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@Chickpea,

I've seen that behavior before and usually it results from an SCHANNEL communication error. So if you are seeing those SCHANNEL errors in the Windows System Event logs we may be able to get that fixed.
ChickpeaSystems Administrator

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Commented:
@scottC well, went to do the update with CU15 and it completely crashed the Exchange install. Now we have no email at all. Got a fun night ahead of me. :)
ChickpeaSystems Administrator

Author

Commented:
So this turned into a nightmare. Had to get Microsoft on the phone and spent over 6 hours with multiple techs. The first resolving the half installed CU15 that we tried to execute. Then a couple more on the OWA as well as exchange web admin console not working.

I am so bleary eyed by the end of it I quit paying attentio what they were doing. Registry edits for the CU15 update and a ton of permission edits in PS for the web based issues. (as well as rebinding certificates multiple times)

Thanks for the suggestions guys but ultimately had to pay to get back up and running. If only I had more time.

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