The PCs are to rendezvous with an escaped prisoner and get him safely across the boarder.
This Skill Challenge can easily be adapted for any scenario where the PCs need to wait in hostile territory for the delivery of any item, person, hostage, etc.
Setup
The lord’s nephew was arrested on trumped up charges and imprisoned while visiting the neighboring country. He is to be executed as a political statement. The PCs are part of a coordinated escape plan. Their job is to meet the prisoner in a remote location and transport him safely and secretly across the nearby boarder.
The prison break is supposed to happen at sundown. The PCs have been instructed to get back across the boarder undetected by sunrise with or without out the prisoner.
At sundown, the DM should roll 2d4 to determine how many hours the PCs wait before the prisoner shows up. If the result is 8 then the escape attempt was unsuccessful. Do not inform the PCs if this happens. Let them decide what course of action to take at sunrise.