A small detour from recaps

I said I could write an entire blogpost on it, so now I will. One of the greatest skills I have learnt from observing/listening to Brennan Lee Mulligan’s DMing is to turn failures into an opportunity to raise the stakes. Zoom in a little closer on the scene and make the next roll twice as important. Make sure to set the difficulty before they roll, ask what their modifier is and let everyone at the table know exactly what you need to roll to pass. Let’s start with an example:
Your player is sneaking past enemy lines to try and get a peak at the general's plans so the rebels might have a chance of winning the war. A soldier turns, certain he heard a sound from behind the tent, they’ve failed their stealth check. He approaches cautiously, you can see the fear in his eyes. He knows you are here, yet his sword trembles.
We honoured the failure, the soldier found them. But now what does he do? Make an insight check with a difficulty of 10 and… oh? They rolled a 6?
Raise the stakes once more.

To get a better vantage you take a step out into the light weapon drawn. A silent stand off broken by another soldier’s question “Everything alright back there Clemens?”.
A second enemy enters the scene, their window of opportunity is closing. It all comes down to this roll. An intimidation check difficulty 15, let this soldier know fear so great that he hesitates. He’ll report back that he saw nothing and pretend none of this ever happened. Annd.. Another 6.
Roll initiative. Another dramatic roll, if they lose this one it’s all over. Another failure? The soldier sprints back before you can react, alerting the camp. They could flee with their mission compromised or double down with a final check. They know the risks, you set the dc. Natural 20. Good thing it was the camp's scheduled security drill tonight.
I can’t believe it all came down to that one important roll.

You have to be careful with this tool. Each failure has to be a step back, each dice roll a more dangerous wager. There is a world here where the player was captured for risking everything on their final check, you have to be ready for that when you offer the deal.
Let them know the stakes and add to the consequences. First seen, then cornered, then outnumbered, then compromised. If there is nothing lost on each roll there was no reason to make one in the first place.