The goal of this article was to assess the effect of modified triple-layer application (MTLA) in conjunction with the active bonding technique on the bond strength of four adhesive systems to dentinal substrate. The adhesives tested were Prime&Bond Universal (PBU), OptiBond Universal (OBU), OptiBond FL (OBFL), and Clearfil SE (CSE). The adhesives were applied according to the following strategies: single active application (A) and triple adhesive layer application including Active–Passive–Passive (APP); AAP; and AAA. The micro-tensile bond strength test was evaluated following 24 h or 6 months of storage. The composite–dentin interface morphology was investigated using scanning electron microscopy. The data were statistically analyzed with a significance level of α = 0.05. At 24 h of aging, all of the factors tested were not significant (p > 0.05) for CSE. For OBFL, OBU, and PBU, statistically higher values were observed for the A technique (p < 0.05). Plus, there were no significant variances between the APP, AAP, and AAA techniques (p > 0.05) for OBFL and PBU. However, for OBU, there were no significant differences between the A and AAA techniques (p > 0.05). After 6 months of aging, the A technique showed statistically higher values when compared to the other techniques (p < 0.01), except for OBFL, where the A and AAA techniques showed promising outcomes. When comparing the bond strength values of 24 h and 6 months, only for PBU, all of the techniques used resulted in bond strength stability over time (p > 0.05). Thicker adhesive layers were observed when MTLA was applied. Only the OBFL adhesive showed the formation of resin tags in all of the modalities tested. The bonding performances of the different application techniques used were material-dependent.