In this work, we study the impact of selection biases on jet structure and substructure observables and separate these effects from effects caused by jet quenching. We use the angular separation ∆R of the hardest splitting in a jet as the primary example of a substructure observable. For illustrative purposes, we first conduct a simplified Monte Carlo study in which it is possible to identify the same jet after quenching in a heavy ion collision and as it would have been if it had formed in vacuum. If we select a sample of jets by placing a cut on their quenched p T (as an experimentalist might do in heavy ion collisions) and, as is possible only in a Monte Carlo study, compare to the same jets unquenched, the ∆R distribution seems to be unmodified by quenching. However, if we select a sample of jets formed in vacuum by placing a cut on their unquenched p T and compare to those same jets after quenching, we see a significant enhancement in the number of jets with large ∆R, primarily due to the soft particles reconstructed as a part of the jet that originate from the wake in the droplet of quark-gluon plasma excited by the parton shower. We confirm that the jets contributing to this enhancement are those jets which lose the most energy, which are not included in the sample selected after quenching; jets selected after quenching are those which lose a small fraction of their energy. Next, we repeat this Monte Carlo analysis using a method that is available to experimentalists: in a sample of jets with a recoiling Z boson, we show that selecting jets based on the jet p T after quenching yields a ∆R distribution that appears unmodified while selecting a sample of jets produced in association with a Z boson whose (unmodified) p T is above some cut yields a significant enhancement in the number of jets with large ∆R. We again confirm that this is due to particles from the wake, and that the jets contributing to this enhancement are those which have lost a significant fraction of their energy. Lastly, we discuss how grooming can be used to vary the importance of the contribution of medium response to the jets.