Hey guys, This post is a PSA for troubleshooting error messages in a hosted environment. Hopefully this will help the next person who may need to dig into why a server request is returning Error 500. Basically the ASP .NET Web API wasn't respecting my web.config settings to turn off custom errors and show the actual error message I was receiving during a POST request. The reason behind this lies with the Web API being designed to run outside of IIS. Yes, self-hosted, which is pretty awesome. One approach that worked for me was to turn on error detail at the global level. I added the following to my Global.asax file: Code: GlobalConfiguration.Configuration.IncludeErrorDetailPolicy = IncludeErrorDetailPolicy.Always; Obviously this required a recompile and push so use with caution. The following blog post by the guys at Los Techies describes the issue in detail and offers up a more elegant solution. That's it. It took me 4 hours to figure out how to get the detailed error message and about 5 mins to copy the missing DLL up to the server. I was using Nuget to pull in some Beta Web API references and missed copying them when I published. Hopefully this will save the next guy some time! (first post)