High pT > 10 GeV elliptic flow, which is experimentally measured via the correlation between soft and hard hadrons, receives competing contributions from event-by-event fluctuations of the low pT elliptic flow and event plane angle fluctuations in the soft sector. In this paper, a proper account of these event-by-event fluctuations in the soft sector, modeled via viscous hydrodynamics, is combined with a jet energy loss model to reveal that the positive contribution from low pT v2 fluctuations overwhelms the negative contributions from event plane fluctuations. This leads to an enhancement of high pT > 10 GeV elliptic flow in comparison to previous calculations and provides a natural solution to the decade long high pT RAA ⌦ v2 puzzle. We also present the first theoretical calculation of high pT v3, which is shown to be compatible with current LHC data. Furthermore, we discuss how short wavelength jet-medium physics can be deconvoluted from the physics of soft, bulk event-by-event flow observables using event shape engineering techniques.