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Trying to think how this should work exactly. done-serve is the thing that sets up the proxy. I suppose it could catch when a 500 occurs and provide a better error message within the console.
In the context of this bug, however, you might not notice this just from looking at the browser console. Perhaps a "better" fix would come from something like donejs/done-serve#22 and provide a front-end UI that reports errors as they occur.
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