Objectives: The development of dental adhesives with enhanced bond strength has assisted minimally invasive dentistry. The aim of this study was to evaluate the fracture load and stress distribution pattern of two retainer designs for posterior cantilever resin bonded fixed dental protheses (RBFDPs). Materials and Methods: Forty human mandibular molars were divided into two groups according to the retainer design; lingual coverage (LC) and occlusal coverage (OC) retainers. Each main group was then divided according to the number of inlay boxes (n = 10); one inlay and two inlay boxes. High translucency (3Y) zirconia was used to manufacture all restorations, and a dual‐polymerizing adhesive resin cement was used for bonding. All specimens underwent 10,000 cycles of thermocycling (5–55°C), 240,000 cycles of dynamic loading (50 N, descending speed v = 30 mm/second, frequency = 1.6 Hz), and failure load test. Both one‐way and two‐way ANOVA tests were used to analyze the data. The four models included in the in‐vitro study are part of the finite element analysis (FEA). When the restorations failed, maximal principal stress values on restorations, enamel, dentin, and luting resin were investigated. Results: A statistically significant (p = 0.018) higher failure load was recorded for OC1 (627.00 ± 153.4 N) than the other groups; (548.0 ± 75.6 N, 521.20 ± 11.3 N, and 509.20 ± 14.9 N for LC1, LC2, and OC2, respectively). With regard to failure mode, one inlay box designs showed more favorable failure pattern than those of two inlay boxes. FEA showed higher stress magnitude transmitted to the tooth structure in models LC2 and OC2. Conclusions: Lingual coverage and occlusal coverage retainers are promising designs capable to withstand the normal occlusal force for cantilever RBFDP in premolar area. The use of two inlay boxes decreased the fracture load of the two retainer designs and increased the stress transmitted to the tooth and resulted in high incidence of catastrophic failure. Clinical Significance: Monolithic high translucent zirconia RBFDP could be considered as a viable treatment option to substitute missing posterior tooth, with improved esthetics and biocompatibility. [ABSTRACT FROM AUTHOR]