The precise origin of Type Ia supernovae (SNe Ia) is unknown despite their value to numerous areas in astronomy. While it is a long-standing consensus that they arise from an explosion of a carbon/oxygen white dwarf, the exact progenitor configurations and explosion mechanisms that lead to SNe Ia are still debated. One popular theory is the double detonation in which a helium layer, accreted from a binary companion, detonates on the surface of the primary star, leading to a converging shock-induced detonation of the underlying core. It has recently been seen in simulations that a helium-rich degenerate companion may undergo its own explosion triggered by the impact from the ejecta of the primary star. We show 2D simulations that approximate a white dwarf undergoing a double detonation which triggers the explosion of the degenerate companion, leading to either a triple or quadruple detonation. We also present the first multi-dimensional radiative transfer results from the triple and quadruple detonation scenario. We find that within a range of mass configurations of the degenerate binary, the synthetic light curves and spectra of these events match observations as well as theoretical models of isolated double detonations do. Notably, double and quadruple detonations that are spectrally similar and reach the same peak brightnesses have drastically different ejection masses and produce different amounts of Si- and Fe-group elements. Further understanding of this scenario is needed in order to determine if at least some observed SNe Ia actually originate from two stars exploding.