Self-adhesion hysteresis has been investigated in crosslinked poly(dimethylsiloxane) (PDMS) lenses using the Johnson, Kendall, and Roberts technique. The experimental conditions involved relatively short contact times for which interchain penetration effects across the interface are minimal. Only lenses that had been extracted in toluene displayed self-adhesion hysteresis. The same lenses demonstrated no adhesion hysteresis when pressed against tethered polystyrene substrates, indicating that hysteresis was caused by surface interactions and not bulk viscoelastic effects. Extraction produces hysteresis by removing the free chains, which normally lubricate the interface, inhibiting the adhesion mechanism. Self-adhesion hysteresis was only observed for networks with a high molecular weight between crosslinks. More tightly crosslinked networks did not display self-adhesion hysteresis, even at extended contact times under load. By inhibiting the hydrosilylation reaction between residual vinyl and silane groups in the PDMS lenses, self-adhesion hysteresis was prevented, suggesting that the formation of chemical crosslinks across the interface caused the observed hysteresis. The molecular weight dependence of the hysteresis can be interpreted in terms of the Lake-Thomas model [1] for fracture in elastomers.