Exploring dark matter via observations of extreme astrophysical environmentsdefined here as heavy compact objects such as white dwarfs, neutron stars, and black holes, as well as supernovae and compact object merger events -has been a major field of growth since the last Snowmass process. Theoretical work has highlighted the utility of current and near-future observatories to constrain novel dark matter parameter space across the full mass range. This includes gravitational wave instruments and observatories spanning the electromagnetic spectrum, from radio to gamma-rays. While recent searches already provide leading sensitivity to various dark matter models, this work also highlights the need for theoretical astrophysics research to better constrain the properties of these extreme astrophysical systems. The unique potential of these search signatures to probe dark matter adds motivation to proposed next-generation astronomical and gravitational wave instruments.