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Mike BroderickFlag for United States of America

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Installed Updates on Exchange Server, Outlook clients will not connect

I applied the 2018-05 Security and Quality Rollup for .NET Framework 3.5 - 4.7.1 (KB4099635) and now my outlook 2013 clients cannot connect to my exchange 2016 server. The outlook clients take forever (about 5 minutes) to load (Loading profile). Once up, all exchange folders are in the status "This folder has not yet been updated" "Trying to Connect" "Disconnected".  When I restore the system state to last night's backup, it works. Unfortunately, windows automatically reinstalled the update and it quit working again.

How do I go about troubleshooting this problem? I dont see any problems in the event log, though there could be and I dont recognize their importance. I found a Health Checker script and ran it. It says I'm on .NET 4.7.1 and the maximum is 4.5.2.

Note: I started the outlook clients in safe mode, same problem.
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Mark Bill
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this is not good.

I would update your outlook client 100% and underlying OS. if problem still persists i would be a bit worried.

At this point i feel this is MS Issue and not EE
use exchange bpa and test connectivity cmdlets impersonating users via autodiscover and any other relevant test cmdlets.

seriously though this is MS Issue all day MS professional services.

Obviously you have options to use a restore of backup in some way or to even look at uninstalling the updates/programs you installed that caused the issues.
i also do not say MS issue lightly BOL
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Mark Bill
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also take a look at exchange server shooter ps script by MS can detect critical issues
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I have restored the system state from last night (again) and everything is working. Fortunately my backup is scheduled for 12AM and the auto update procedure started around 4:30AM. I hid the update rollup so it would not automatically install again. I also made another system state save that I am setting aside. Waiting for Microsoft to fix what they broke is reasonable (sooner or later somebody important will demand this gets fixed and MS will fix it).
Good
In the results of running the Health Checker script it mentioned that I havent applied Cumulative Updates for over 2 years. I assumed the Exchange updates were applied along with windows updates. When I applied the latest Cumulative Update, applying the rollup update did not cause problems.

The Health Checker script mentioned some other things I am looking into. For anybody interested, here is where you can download it:

https://gallery.technet.microsoft.com/Exchange-2013-Performance-23bcca58

Thanks to both of you for all of your help.
TY I deliberately avoided restoring a backup to find out what the issue is here, resolution came across because MS will not deal with you unless these steps are completed.