Discussion moved from Community Interface Help (totally wrong area for this) to Web Gateway for better support.
Not sure how Checkpoint is working but here is my assumption.
As it is an SSL VPN, it will require a client certificate authentication, which MWG is not able to provide as it doesn't know the clients cert. The following possibilities come to mind:
Disable SSL Scanner for this site
Create and event that uses "Enable HTTP Tunnel" to tunnel all data through the gateway based on the destination or pair it with the property "SSL.Server.Handshake.CertificateIsRequested" so that you get a rule that says,
If the server requests a client cert, tunnel all data.
As said, only a quick thought.
Same error my customer is getting "establish connection to SSL Network Extender gateway. Try to reconnect" when he try to connect his checkpoint SSL network Extender. Can any body will help here please. This is working fine from Internet but not connecting through Intranet. Traffic is going through Web Gateway.