This study tested the hypothesis that long-term durability of resin bonds to dentin is directly related to the nanoleakage of dentin bonding systems. Extracted human third molars were ground flat with 600-grit SiC paper under running water to expose middle dentin. Clearfil Liner Bond 2V (LB2V) or Fluoro Bond (FB) was applied to dentin surfaces according to the manufacturer's instructions. A crown was built-up with Clearfil AP-X resin composite, and the specimens were stored in water for 24 hours at 37 degrees C. The bonded assemblies were vertically sectioned into approximately 0.7 mm thick slabs and trimmed for microtensile bond test. All slabs were immersed in individual bottles of water at 37 degrees C, which was changed every day. Specimens were incubated for one day, and three, six, and nine months, and at the specified time period, they were randomly divided to two subgroups: 50% AgNO3 and the control. In the 50% AgNO3 subgroup, the slabs were immersed for one hour in 50% AgNO3, followed by exposure in a photo-developing solution for 12 hours just prior to debonding. The specimens in the control subgroup were soaked in water until debonding. Then, all specimens were subjected to microtensile bond testing. The debonded specimens of the AgNO3 subgroup had micrographs subjected to image analysis by NIH Image PC (Scion, Fredrick, MD, USA), and the area of silver penetration was quantitated. The bond strength data and silver penetration areas were subjected to two- and three-way ANOVA and Fisher's PLSD test at the 95% level of confidence. Regression analysis was used to test the relationship between bond strengths and the silver penetration area at each time period. For both adhesive systems, the bond strengths gradually decreased over time, although there were no statistically significant differences in the FB bond strength among the four time periods tested (p>0.05). Silver penetration in specimens bonded with LB2V and FB gradually increased over time. Regression analysis showed a higher correlation between bond strength and silver penetration at 9 months for specimens bonded with LB2V (R2=0.844) than at shorter time periods. The authors speculate that hydrolytic degradation within the hybrid layer gradually increased due to water penetration through nanoleakage channels, resulting in lower bond strengths and interfacial failure after as little as nine months.