Issues Accessing Secure Sites

Our current setup is:

1x Sophos Management Appliance SM2000

2x  Sophos Web Appliance WS1100

We have a lot of issues concerning secure sites.

I am currently in talk with sophos support too, but support is so terrible. One or two email per day...when will this be solved if its going to be this slow?

See screenshots below.

 This screenshot shows that yahoo mail is accessible when sophos proxy is not used for the secure connection. But if sophos proxy is used in secure connection using port 8080, yahoo mail wont open asa well as gmail and other secure sites.

Below error is when Sophos Proxy is used in Yahoo Messenger.

 ***  'COMPONENT_TYPE_WININET' value: '12031' ***

Checking virtual IP servers...

[VIP Raw] Connecting to Virtual IP server 172.20.32.197... [PASSED]

[VIP Raw] Sending HTTP request to the server... [PASSED]

[VIP Raw] Receiving response... [PASSED]

[VIP Raw] Checking HTTP response code... [PASSED]

[VIP Raw] Parsing connection server IP address... [PASSED]

[VIP Raw] Connecting to Virtual IP server 172.20.32.197... [PASSED]

[VIP Raw] Sending HTTP request to the server... [PASSED]

[VIP Raw] Receiving response... [PASSED]

[VIP Raw] Checking HTTP response code... [PASSED]

[VIP Raw] Parsing connection server IP address... [PASSED]

[VIP Raw] PASSED *** 98.136.48.83 ***

Checking connection servers...

[CS Raw] Connecting to connection server port '5050'... [PASSED]

[CS Raw] Sending port check command... [PASSED]

[CS Raw] PASSED

Checking login servers...

[Login] FAILED