@PureShipper Well, I think this is the root of the problem, which is that 残念 just doesn't have a real 1:1 translation. It's main use case is in a phrase which has a similar use case to the common English phrase, "How unfortunate," or "Unfortunately,..." which is why 'unfortunate' is a common translation for it, but as you say, the literal meaning is closer to something like 'regrettable' rather than unfortunate (from my experience at least).