Perhaps there are some rules out there already on how to handle these kinds of hostage situations. I have yet to see anything satisfying to me . . . .
In my campaigns we make fairly regular use of the d20 3.5 Coup de grace rules. Unfortunately, these don’t seem to capture the “movie-like” tension created with the bad guy has a knife to the through of his hostage, using them as a human shield.
Allow me to elucidate: ;^)
There are traditional two levels of attacking a helpless target:
(1) Normal attack against an immobilized (bound, sleeping, etc.) target
- This requires a partial action, does normal damage (plus sneak attack if applicable).
- The target has a minus 9 to their AC. (-4 penalty, plus a Dexterity reduced (max -5) for a total penalty of -9)
(2) Coup de grace attack
- This requires a full-round and provokes an attack of opportunity. The attack of opportunity is resolved before determining the results of the coup de grace attack.
- It does provide and automatic hit, and is an automatic critical. In fact, the target must make Fortitude save vs. DC 10+total damage dealt, or die on the spot. (Quite potent really---as it should be)
The problem is with that attack of opportunity. High level characters have a good possibility of attacking and killing a villain as they try to make their fell blow.
Thus leading to the rational of:
(3) Readied coup de grace attack
This forces players into some other creative tactics to negotiate hostage situations: bluffing, feinting, diplomacy, distractions, perhaps even (heaven forbid) giving into the villains demands.
If players still want to risk attacking the hostage taker—remember those rules about striking cover. If your villain is using their victim as a shield (i.e., standing behind them), and your players say “I was to shoot him in the eye with my bow.” Remember, the villain gets a bonus to his AC relative to how much of his body the players can see. If they miss by an amount less than or equal to his bonus (in other words—if they would have hit him if he didn’t have the bonus) they strike the target. (Also bad news for the victim.)
I imagine it only takes accidentally killing one damsel in distress before your players start thinking a little harder about those hostage situations . . .

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