Many patients experience vertical root fractures, and clinicians often consider conservative treatment options like reattaching the fractured root segments. The study investigated the impact of different bonding agents on the fracture resistance of rebonded vertically fractured teeth with various alveolar bone defects. Human premolar teeth with a single root were sectioned and reattached using dual-cure resin cement (DCRC), resin-modified glass ionomer (RMGI), and cyanoacrylate. The reattached teeth were then restored with a resin fiber post, composite resin core, and full veneer metal copings. These teeth were embedded in acrylic blocks with angular, V-shaped, and step-shaped bone defects to simulate various alveolar bone conditions. After subjecting the samples to thermal cycling, the fracture resistance was evaluated using a universal testing machine. Teeth samples reattached with RMGI exhibited a higher average fracture resistance. The study also found that DCRC proved to be an effective bonding agent for VRF teeth. However, cyanoacrylate-rebonded teeth exhibited the lowest fracture resistance. The V-shaped defects had a significant impact on the fracture resistance of reattached VRF teeth, with largely unfavorable fractures observed in these cases. Predominantly favorable fractures were observed in the teeth treated with RMGI. The fracture loads in both RMGI and DCRC groups exceeded the expected masticatory load.