Solution
This behavior is expected and happens due to a LabVIEW limitation.
The way remote debugging works is by loading the source VI on the debugger side that match the VIs on the execution side and syncing execution info between them. Since the execution side may be a different platform than the debugger side, the debugger side can't be used to determine errors and LabVIEW does not have a way to sync errors from execution to debugger. End result is that the debugger doesn't know what the errors are on the execution side. It only knows that the VI is broken.