Competing pathways in catalytic reactions often involve transition states with very different charge distributions, but this difference is rarely exploited to control selectivity. The proximity of a counterion to a charged catalyst in an ion paired complex gives rise to strong electrostatic interactions that could be used to energetically differentiate transition states. Here we investigate the effects of ion pairing on the regioselectivity of the hydroarylation of 3-substituted phenyl propargyl ethers catalyzed by cationic Au(I) complexes, which forms a mixture of 5- and 7-substituted 2H-chromenes. We show that changing the solvent dielectric to enforce ion pairing to a SbF6- counterion changes the regioselectivity by up to a factor of 12 depending on the substrate structure. Density functional theory (DFT) is used to calculate the energy difference between the putative product-determining isomeric transition states (Delta Delta E-double dagger) in both the presence and absence of the counterion. The change in Delta Delta E-double dagger upon switching from the unpaired transition states in high solvent dielectric to ion paired transition states in low solvent dielectric (Delta(Delta Delta E-double dagger)) was found to be in good agreement with the experimentally observed selectivity changes across several substrates. Our calculations indicate that the origin of Delta (Delta Delta E-double dagger) lies in the preferential electrostatic stabilization of the transition state with greater charge separation by the counterion in the ion paired case. By performing calculations at multiple different values of the solvent dielectric, we show that the role of the solvent in changing selectivity is not solely to enforce ion pairing, but rather that interactions between the ion paired complex and the solvent also contribute to Delta(Delta Delta E-double dagger). Our results provide a foundation for exploiting electrostatic control of selectivity in other ion paired systems.