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If the rails addon crashes on startup, there's no indication of where the problem is. There's the long logs in the "Output" tab, but you'd have to know to look there, and they can be rather large especially with the long backtraces common with rails applications.
I coded up a simple POC to parse the exception text for a meaningful message, and last source location under the workspace, and send a Diagnostic: #649 so that the problem is revealed in the "Problems" tab under the editor. It's not necessarily pretty, and might not handle all situations where there's a runtime error, and it doesn't seem like it'll result in the rails addon being retried once it fails once (even if the source of the problem is fixed). But, it might provide a good jumping off point for someone more familiar with this project to take on.