On Survivor: Palau, Jenn's friendship/romance with fellow castaway Gregg Carey was largely responsible for her success in the game. For a time, Jenn, Gregg, Ian Rosenberger, Katie Gallagher, and Tom Westman (the eventual winner) had a solid alliance and appeared to be headed to the Final Five together. However, the close bond between Jenn and Gregg proved to be their undoing. While Jenn, Gregg, and Katie enjoyed a reward together, Tom and Ian, fearful of the tight bond between Jenn and Gregg and the possibility that Katie would betray them, conspired with Caryn Groedel to vote off Gregg.

Without her main ally, Jenn scrambled to stay in the game. She was briefly part of a women's alliance with Katie and Caryn, which ended because Katie and Caryn did not get along. (An earlier attempt to form a women's alliance also failed, partly because Jenn refused to ally with perceived threat Stephenie LaGrossa, whom Jenn thought would be trouble down the road.) After the Koror tribe voted out Caryn, in order to save herself, Jenn strategized and convinced Tom that Ian was planning to vote him out. Jenn's strategy worked; Tom and Jenn voted against Ian at the next tribal council. However, because Katie and Ian voted against Jenn, the votes were deadlocked and Jenn and Ian had to participate in a tie-breaker. The tie-breaker involved building fire, and Ian won by starting his fire faster than Jenn. With that, Jenn became only the second player in Survivor history to reach the Final Four but lose without being voted out. (Paschal English, the fourth place finisher in Survivor: Marquesas, lost a different type of tie-breaker and left the game without being voted out.)