if there are invisible or unknown consequences for failure then Flipping a DP should be a requirement, to give the player the safety of knowing that your not being nasty, and that there will be opportunity for a good thing to happen in the future because they risked something now.
Sure, but remember that the dice are a contract, and the player has the right to refuse the roll if they don't like them odds. So sayeth Jay Little on the Order 66 podcast, amen. In that case, the PC may not know how much trouble he or she is in, but the player knows.