How to handle checks that just HAVE to succeed?

Determine degrees of success.

A great tracking roll will get them unnoticed right to the bad guy's lair. Say DC 20+

An OK roll (DC 10+) will get them there, but it might take longer than they'd hoped, meaning the assault will be tougher, the guards more prepared and vigilant, etc.

A poor roll (less than DC 10) gets them noticed, and possibly ambushed or misled. Followup must be done to find the lair - Gather Info, bribery, etc.

That's how I'd handle it.
 

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