The aim of this study was to evaluate the bond strength of the calcium silicate-based sealer (CSS) modified with the silver nanoparticles (AgNPs) using the single-cone technique (SC) and the continuous wave condensation (CWC) technique, measured by a universal testing machine. The AgNPs and the modified sealers were characterized by scanning electron microscopy and transmission electron microscopy. One hundred single-rooted extracted human permanent teeth with a single root canal were cleaned and shaped with a Protaper Next system. The teeth were randomly divided into four groups (n = 25) as follows: Group 1, canals were obturated using the SC technique with TotalFill® BC Sealer. Group 2, canals were obturated using the SC technique with TotalFill® BC Sealer mixed with AgNPs. Group 3, canals were obturated using the CWC technique with TotalFill® HiFlow BC Sealer. Group 4, canals were obturated using the CWC technique with TotalFill® HiFlow BC Sealer mixed with AgNPs. After two weeks, 1 mm-thick dentin slices were cut and exposed to a push-out bond strength test using a universal testing machine. Specimens were examined under a digital microscope to determine the mode of failure. Statistical analysis was performed using ANOVA and Tukey multiple comparison tests (p < 0.05). The nanoparticle characterization revealed a spherical morphology with no obvious aggregations. The results showed that group 4 had the highest dislodgement resistance compared to all groups (p < 0.05). Group 4 was significantly higher in push-out bond strength value than group 1 (p < 0.001) and group 3 (p < 0.003), but not significantly higher than group 2. Cohesive failure was the most prevalent failure mode among all groups. It can be concluded that the incorporation of silver nanoparticles into the calcium silicate-based sealer significantly increased the bond strength. The warm obturation approach demonstrated significantly higher resistance to dislodgment as compared to the single-cone technique.