A carefully controlled, custom-built adhesion testing device was developed which allows a precise, short dwell time on the order of milliseconds to be applied during a contact adhesion experiment. The dwell time dependence of the adhesive strength of crosslinked poly(dimethylsiloxane) (PDMS) in contact with glass and uncrosslinked styrene butadiene rubber (SBR) in contact with glass and with itself was tested with a spherical probe in a confined Johnson-Kendall-Roberts (JKR) geometry. Analysis of the contact images revealed several unique separation mechanisms which are dependent on dwell time and interfacial properties. PDMS-glass interfaces show essentially no dependence of adhesion on the dwell time while the adhesive strength and separation mechanisms of SBR interfaces are shown to vary drastically for dwell times ranging from 40 to 10?000 ms. This influence of dwell time is particularly pronounced for polymer-polymer (SBR-SBR) interfaces. Observations of cavitation due to trapped air pockets in the center of the contact at very short contact times illustrate a transition between a defect-controlled debonding and an interface-controlled debonding which has not been previously reported.