I'l go against the grain here…

Don't ever fudge rolls or help the player. It will rob them of their agency, and it will probably piss off other players. Besides, not having risks and consequences will make them into careless players at best or actually turn them into murderous cretins.

Changing the system may help with the probabilities of having to deal with such a situation but that may not be feasible for every game. And even in the best system, you will find yourself rolling horribly every once in a while.

So my core advice is, roll with it but make an awesome story out of failure. Make sure that the player's failure is not in vain, and is definitely spectacular. Use it as a hook to introduce plot complications, add interesting twists to the story that will challenge all the players. Turn it into something memorable.

That way, your players will probably ask for more failures.

I'l go against the grain here…

Don't ever fudge rolls or help the player. It will rob them of their agency, and it will probably piss off other players. Besides, not having risks and consequences will make them into careless players at best or actually turn them into murderous cretins.

Changing the system may help with the probabilities of having to deal with such a situation but that may not be feasible for every game. And even in the best system, you will find yourself rolling horribly every once in a while.

So my core advice is, roll with it but make an awesome story out of failure. Make sure that the player's failure is not in vain, and is definitely spectacular. Use it as a hook to introduce plot complications, add interesting twists to the story that will challenge all the players. Turn it into something memorable.

That way, your players will probably ask for more failures.