To assess the bond strength and the hybrid layer (HL) micro-morphological characteristics at the cement-dentin interface (CD-i) between root canal walls and two adhesive resin cements [self-etch (SERc) and self-adhesive (SARc)] in root-canal-treated (RCT) and naturally aged retreated teeth (RCR-T). Vital (n = 16) and RCT (n = 16) teeth were, respectively, endodontically treated or retreated. Fiber posts were luted either with SERc (Clearfil Universal Bond Quick + DC Core Plus) or SARc (iCEM). Samples were then sectioned into 1 mm thick slices perpendicular to the fiber post and submitted to push-out bond strength test. Vital (n = 4) and RCT (n = 4) first maxillary molars were also selected and prepared to evaluate CD-i morphology through confocal laser scanning microscopy (CLSM). Three-way analysis of variance (ANOVA) and Tukey post-hoc tests were assessed to statistically analyze the obtained data (p 0.05). Bond strength was significantly jeopardized in retreated teeth and in the root apical half, while the cements had no significant influence. Most failures occurred between dentin and resin cement. HL thickness was also hindered in retreated teeth. iCEM produced a thinner HL compared to SERc. Resin tag formation was significantly hampered in the root apical half. SARc performed as well as SERc on aged RCT radicular dentin. Clinicians can rely on simplified one-step luting systems when adhesion is required in unfavorable substrates such as the root canal post space of aged RCT teeth.