Spent the evening troubleshooting this but couldn't get to the bottom. I followed the detailed step by step config guide in the wiki and have my "external app" and "context" settings configured per the wiki. Whenever I hit my RoR app I get a 404 error but the RoR welcome page shows up fine. I checked the main server log files error.log and stderr.log and nothing is out of the ordinary, stderr.log shows that one ENV warning but nothing else. The vhost log files are totally clean and there is nothing in my RoR app development.log file. I can run dispatch.lsapi from the command line and no errors are displayed. Only thing I noticed is when I have the doc root under the general tab in the vhost config set to the same as the "Location" field for my Rails context I get an error in the logs saying the context is invalid and because for some reason it appended another "public" to the end of the file path. But when I change the "Location" field in the Rails context so it references one folder above "public" then this error goes away. Maybe I'm missing something obvious here...?