Sending 64-bit Apps to a 32-Bit OS

I have a project where I’m creating 32-bit and 64-bit Windows builds so I have both running in a VM and I send them from my Mac for testing. It seems weird that if I send a 64-bit version to a 32-bit OS I get a crash and an error in the IDE saying something unexpected happened with the remote app.

I expect that the IDE would a) either force the 32-bit build (silently) or b) tell me beforehand that it can’t send a 64-bit build to that OS. Is the Remote Debugger not that smart?

2018 R1.1 and Debugger Stub 2.3.1.

I’ve seen this happen on Windows for sure and maybe in Linux. Anyone else seen this?