The WinRM client cannot process the request. It cannot determine the content type of the HTTP response from the destination computer after CU10 Upgrade

Cannot Access Exchange 2016 Exchange Powershell after CU Update. Users Outlook cannot connect, OWA and ECP cannot connect either.

I issued the command Get-ExchangeServer | Format-List Name, Edition, AdminDisplayVersion to verify the current Exchange CU version which is CU3 15.1.544.27 and wanted to update to CU10.

I use the Admin Power Shell to do the update, however, when I ran the following command, d:>setup /m:upgrade /IAcceptExchangeServerLicenseTerms

For some reason, it was indicating that i was upgrading CU 3 and not CU 10, so i let it install successfully and thats where the problems started when I tried to connect to the Exchange Admin Powershell.

Users cannot access mailboxes, OWA doesn't work and ECP doesnt work. I tried to access the Exchange Admin Powershell with another account and same issues.

VERBOSE: Connecting to FQDN.
New-PSSession : [FQDN] Connecting to remote server FQDN failed with the following
error message : The WinRM client cannot process the request. It cannot determine the content type of the HTTP response
from the destination computer. The content type is absent or invalid. For more information, see the
about_Remote_Troubleshooting Help topic.
At line:1 char:1
+ New-PSSession -ConnectionURI "$connectionUri" -ConfigurationName Microsoft.Excha ...
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    + CategoryInfo          : OpenError: (System.Manageme....RemoteRunspace:RemoteRunspace) [New-PSSession], PSRemotin
    + FullyQualifiedErrorId : -2144108297,PSSessionOpenFailed
Marlon ChungAsked:
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Saif ShaikhServer engineer Commented:
I think your upgrade did not went well. It's a failure after looking at the errors you are getting.

Try to check the exchange setup logs on C drive for more information.

Also check the registry location: screenshot attached.

If the setup did not completed properly there might be a watermark key created.

1) Delete the installation watermark, and you can do that from here:

2) The user account you are running it with has local admin permissions (not required but something I typically do), along with being a member of the Enterprise Administrators group. This is critical. If this is not the first Exchange 2013 server in the organizational management group as well (if it is your first E15 server then ignore the org management group membership).

3) IF your machine has UAC (User Access Controls) you HAVE to right click the Setup.exe file for Exchange 2013 CU3 and select "Run as Administrator". You can check if UAC is running by doing the following:

Try this again, and if it fails again please post the logs.
Marlon ChungAuthor Commented:

I did a live remote session with Viktor Grant late last night at around midnight PST and sure enough, it was a problem with the install. I initially did a unattended install via the Admin Powershell and i watched it go through all the services and it finalized successfully, so to me i didn't have any reason to think the install was incomplete. The funny thing was at the start of m:/upgrade option, it came up saying the upgrade was for CU3, so that should have been a red flag, but I continued anyway.

With Viktor onboard we ran the upgrade via setup/GUI and it went well. the ony thing that was stubborn on starting was the transport service which Viktor fixed, so kudos to him on that.

Mail flow is working now and all good to go.

I appreciate your input and you also nailed it on the incomplete install to begin with.
Marlon ChungAuthor Commented:
Solution was to reinstall Exchange 2016 CU10. This time, setup  was launched via the Setup Wizard GUI by double clicking on the setup.exe

Not sure why the Admin Powershell didn't work in the first place with the unattended  d:>setup /m:upgrade /IAcceptExchangeServerLicenseTerms command.

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Marlon ChungAuthor Commented:
Viktor Grant well done on the support and fixing the CU10 Upgrade and fixing the transport issue
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