Lack of Support for Yosemite
To connect with Yosemite, use the iOS mobileconfig setting on AirPennNet-Help.
Problems with Version 5.0.115 Resolved
Problems with version 5.0.115 of Cloudpath's XpressConnect, released on 8/13/14, have been resolved -- Android 4.4 devices should no longer have trouble connecting to AirPennNet.
To confirm which version of XpressConnect you are using, check your Android device's Application Manager.
If you are using the new version, and have trouble connecting to AirPennNet you may need to clear out your XpressConnect settings before you can successfully connect using the older version 5.0.110. See these instructions on clearing your settings.