(1) Background: This study investigated the effect of the adhesive layer thickness and the length of resin tags on dentin bond strength of five universal adhesives applied in self-etch mode. (2) Methods: One hundred and fifty extracted human third molars were used. Five different universal adhesives were applied in self-etch mode on the dentin surface. Half of the specimens were subjected to an aging procedure for six months. A shear bond strength (SBS) test was performed and the results were statistically analyzed with a t-test and one-way ANOVA test. Scanning electron microscopy (SEM) was executed to measure the adhesive layer thickness and tag depth. (3) Results: No statistical differences were found between the five adhesive systems after a 24 h storage period, regardless of layer thickness and tag depth (p < 0.05). After 6 months of aging in water at 37 C, Iperbond Max and Scotchbond Universal preserved the bond strength over time (p < 0.05), whilst the SBS of Iperbond Ultra, FuturaBond M+, and Ibond Universal decreased significantly after the aging period. No relation was observed between the adhesive thickness or tags’ length on SBS. (4) Conclusions: Within the limitation of this study, the stability over time of the bond strength of universal adhesives depends on their compositions regardless of the adhesive layer thickness and/or tags’ length.