Hi JPoli,
Does the issue happens under certain network conditions or it happens wherever you go. If so, please click on the link below to troubleshoot the issue.
http://support.microsoft.com/kb/956531
If not, please run a Outlook Anywhere test in Remote Connectivity Analyzer through https://www.testexchangeconnectivity.com/. Please select Outlook Anywhere (RPC over HTTP) under Office 365 and click Next to perform a test. Please capture a screenshot of the test result.
Thanks,
Yang Yu