In some cases it's impossible to activate or update AirServer because of firewall or network port restrictions. In order for this to work you have to make sure that activation.airserver.com, api.airserver.com and download.airserver.com are accessible through HTTPS (port 443) in your proxy.

If a direct connection cannot be established then an attempt will be made to see if the current user has proxy settings set for Internet Explorer, if that is not the case (as it might be if the installer is being automated) then it will attempt to use DHCP and/or DNS A record to obtain the proxy settings. If you have a PAC script make sure that the identity running the installer has enough rights to access it if it is on a network share (NTML/Negotiate authentication).

If you are having trouble configuring proxy settings for the user that is doing the actual installation (i.e. the user context that GPO or SCCM launches msiexec.exe under) then they might want to advertise proxy using DHCP or DNS. We would recommend allowing the previously mentioned addresses to not require proxy (i.e. create a valid route for it). 

Alternatively we would suggest reading the following:

• Automatic Discovery for Firewall and Web Proxy Client
• “Automatically Detect Settings” Does Not Work if You Configure DHCP Option 252
• SRSP1_H_Create252