A three-dimensional cavity design was used to study the morphology of dentin in vitro both after dentinal pretreatment and after restoration failure (debonding). Dentinal bonding agents that require removal of the smear layer (third generation), as well as those that depend on attachment to the smear layer (second generation), were included. Results indicated cohesive failures within both the dentinal bonding agents and the smear layer in second-generation systems. Dentinal conditioners for the third-generation dentinal bonding agents and for an as-yet unclassified agent were effective in removing smear layer debris from the dentinal surface, but they varied in the degree to which they opened the dentinal tubules. Differences in morphology of the dentinal surface following debonding of the restoration were attributed to differences in chemical composition among the agents examined.