Hi
couple things to check.
1. That the connection isn't being diverted or intercepted anywhere. https over socks would be intercepted to the WWW proxy if the WWW proxy was intercepting port 443. The current version of WinGate 7 doesn't support this, so you should ensure the WWW proxy is not intercepting port 443.
2. MTU. We find sometimes (relatively often actually) that SSL doesn't like path MTU discovery. If the internet connection MTU is lower than the adapter MTU on the WinGate proxy, then we've seen problems with https connections before.
To check MTU, use ping.exe from the command line. Normal MTU is 1500, to test if 1500 bytes will go over your internet connection without fragmenting, use
ping
www.microsoft.com -f -l 1472
If you get a response saying the packet must be fragmented (which you may well see if you're on a PPPoA or PPPoE connection) you may need to then adjust the adapter MTU on your WinGate computer for the internet-facing adapter.
Failing all of that, we can have a look remotely and I'd recommend a packet capture to see what is going on. If you need to take that approach, send us an email to
support@wingate.com with teamviewer or other remote access details.
Regards
Adrien de Croy