If you are still having problem then you will want to turn on Debug logging for the Servers/Services you are connecting to in WinGate.
If you are connecting via WinGate's POP3 / SMTP Server (which I presume) then turn on the debug logging in there.
If you are connecting via WinGate's POP3 / SMTP Proxies then turn on the debug logging in there.
Once the debug logging is on then recreate the error by trying to connect to the email server / proxy and then review the extra details in the relevant log files within C:\Program Files\WinGate\Logs
If you are still having problems then you may want to create a support ticket and send in the following details and reference this forum post:
1. WinGate Registry.
GateKeeper --> Options menu --> Advanced --> Save Registry
2. WinGate Config Report
GateKeeper --> Options menu --> Advanced --> Save Config Report
3. ipconfig/all from the WinGate Server
(Windows) Start menu --> Run --> cmd --> ipconfig/all >> C:\ipa.txt
http://support.qbik.com/index.php?_a=tickets&_m=submit