Shock/turbulent-boundary-layer interactions (STBLIs) are ubiquitous in high-speed flight and propulsion applications. Experimental and computational investigations of swept, three-dimensional (3-D) interactions, which exhibit quasi-conical mean-flow symmetry in the limit of infinite span, have demonstrated key differences in unsteadiness from their analogous, two-dimensional (2-D), spanwise-homogeneous counterparts. For swept interactions, represented by the swept–fin-on-plate and swept–compression–ramp-on-plate configurations, differences associated with the separated shear layers may be traced to the intermixing of 2-D (spanwise independent) and 3-D (spanwise dependent) scaling laws for the separated mean flow. This results in a broader spectrum of unsteadiness that includes relatively lower frequencies associated with the separated shear layers in 3-D interactions. However, lower frequency ranges associated with the global “breathing” of strongly separated 2-D interactions are significantly less prominent in these simple, swept 3-D interactions. A logical extension of 3-D interaction complexity is the compound interaction formed by the merging of two simple interactions. The first objective of this work is therefore to analyze the more complex picture of the dynamics of such interactions, by considering as an exemplar, wall-resolved simulations of the double-fin-on-plate configuration. We show that in the region of interaction merging, new flow scales, changes in separation topology, and the emergence of lower-frequency phenomena are observed, whereas the dynamics of the interaction near the fin leading edges are similar to those of the simple, swept interactions. The second objective is to evolve a unified understanding of the dynamics of STBLIs associated with complex configurations relevant to actual propulsion systems, which involve the coupling between multiple shock systems and multiple flow separation and attachment events. For this, we revisit the salient aspects of scaling phenomena in a manner that aids in assimilating the double-fin flow with simpler swept interactions. The emphasis is on the influence of the underlying structure of the separated flow on the dynamics. The distinct features of the compound interactions manifest in a centerline symmetry pattern that replaces the quasi-conical symmetry of simple interactions. The primary separation displays topological closure to reveal new length scales, associated unsteadiness bands, and secondary flow separation.