The most common reason that might cause this error is compatibility. There is a high chance this software isn't compatible with Windows Server 2013 or the file is not allowed to communicate with Internet. Check your firewall and make sure EasyWeather is allowed to send data. You will need to add an exception in the firewall and add the executable file to use the network adapter to reach the servers where you have to upload.
It's also better to define a rule by PORT. This way you will know for sure that app will communicate with the servers.