We are sorry for delayed answer.
When configuring Outlook to use secured connection, please make sure to have the AVG Outlook plugin installed (not the Personal E-mail scanner plugin). More information can be found here.
Also, if you are using AVG Firewall, we recommend regenerating its configuration to make sure the Real Player is not blocked by the firewall:
1. Open the AVG user interface and click the Firewall component.
2. Click the Regenerate configuration button and follow the wizard.
As recommended by Bob, disabling AVG temporarily or uninstalling it temporarily will allow you to verify whether the issues are caused by AVG indeed. We recommend disabling individual AVG components to find out which one could be causing the problem. If the network connectivity issues appear to be indeed caused by AVG, please make sure to have only one active security software installed at a time as they may interfere.
Should the issue persist please contact AVG customer care for further investigation (diagnostic data from your computer will be required, most likely).