I have R2-D2 crew. I have flipped a Munitions Failure which did nothing to me.

Am I allowed to repeatedly select that same card over and over (if I roll a hit when using R2-D2 in the future)? It's on Vassal, so I can't exactly shuffle the dealt damage cards (I have other dealt damage).

Yes/NO!

R2D2 is supposed to turn over a RANDOM face-down damage card. This means you can't specifically pick one, which you happen to know what it is, over something else that you may, or may not, know what it is.

You can repeatedly turn over Munitions Failure but ONLY if that is the random card you keep getting told to turn over. YOU get to have no part in the selection and neither does your opponent. Now I don't know how to randomly select things on Vassal but if it does random dice and randomly selects which cards you'd get in the first place their should be a mechanic for randomly selecting which card R2D2 will turn up.

Well, poor Chewie bit the dust in the next round, so we didn't have to resolve it.