Imaging Atmospheric Cherenkov telescope (IACT) searches for dark matter often perform observations in "wobble mode," i.e., simultaneously collecting data from the signal region and from a corresponding background control region. This observation strategy is possibly compromised in scenarios where dark matter annihilates to long-lived mediators that can traverse astrophysical distances before decaying to produce the gamma rays observed by the IACTs. In this Letter, we show that this challenge comes with several interesting features and opportunities: in addition to signal contamination in the background control region, the gamma-ray spectrum changes with the observing direction angle and typically exhibits a hard excess at high energies. Such features represent a significant departure from the canonical picture and offer novel handles to identify a dark matter signal and to extract underlying dark matter parameters.