One of the major questions facing particle physics is whether electroweak symmetry breaking is natural. LHC searches for new particles and measurements of Higgs properties have increasingly disfavored this possibility. I will discuss two fronts on which theory can help LHC experimentalists in searching for an answer. The first is by proposing precision techniques to make existing search channels more sensitive. The second is by proposing new search channels and simplified models to expand the range of theories being probed. I will use the stop squark in stealth SUSY models as an example. I will also discuss some aspects of split supersymmetry as a possible unnatural model, highlighting the interplay between astrophysics, cosmology, and collider physics.