We consider the indirect detection of dark matter that is captured in the Sun and subsequently annihilates to long lived dark mediators. If these mediators escape the Sun before decaying, they can produce striking gamma ray signals, either via the decay of the mediators directly to photons, or via bremsstrahlung and hadronization of the mediator decay products. Using recent measurements from the HAWC Observatory, we determine model-independent limits on heavy dark matter that are orders of magnitude more powerful than direct detection experiments, for both spin-dependent and spin-independent scattering. We also consider a well-motivated model in which fermionic dark matter annihilates to dark photons. For such a realistic scenario, the strength of the solar gamma ray constraints are reduced, compared to the idealistic case, due to the fact that the dark matter capture cross section and mediator lifetime are related. Nonetheless, solar gamma ray constraints enable us to exclude a previously unconstrained region of dark photon parameter space.