Windows Updates

[britt1kj]

Checkpoint Community,

Trying to update all my windows servers (2016) behind a checkpoint r80.20...

Looking to get these working and thought it would be adding an easy service for windows update. 

But no matter what I try, I get something blocking" 

"WinHttp: SendRequestToServerForFileInformation failed with 0x80072ee2; retrying with default proxy.
Send request failed, hr:0x80072ee2
Library download error. Error 0x80072ee2. Will retry. Retry Counter:2
Send request failed, hr:0x80072ee2
WinHttp: SendRequestToServerForFileInformation failed with 0x80072ee2; retrying with default proxy." 

These worked very easily before the appliance was there. Is there something at the host level that needs to be done? 

Or Maybe even on the checkpoint Server.

Any help would be deeply apprecaited

[AlejandroH]

Do you have HTTPS inspection turned on?  What are some blades turned in that network segment?

[britt1kj]

HTTPS inspection turned on?

It is turned off 

We Have the following turned on : Firewall, Application Control, URL Filtering, IPS 

[PhoneBoy]

What do you see on the firewall logs when the servers try to update?