Immediate implant placement and delayed implant placement remain two central strategies in contemporary implant dentistry, particularly in compromised extraction sites where the biological environment is suboptimal and the predictability of integration is less certain. Compromised extraction sites often present with periodontal defects, periapical pathology, trauma-related bone loss, thin buccal plates, or ridge deficiencies. These conditions introduce complexity and clinical uncertainty, prompting debate regarding the ideal timing for implant placement. Over the past three decades, research has shifted toward understanding how host biology, surgical technique, defect morphology, and adjunctive biomaterials influence outcomes in both immediate and delayed approaches. The immediate placement protocol offers several advantages, such as reduced treatment times, preservation of soft-tissue architecture, and potentially improved patient acceptance. However, these benefits may be counterbalanced by a higher risk of early implant failure in the presence of infection, inadequate primary stability, or significant bone dehiscence. In contrast, delayed placement provides clinicians with optimal healing conditions and opportunities for ridge augmentation but prolongs treatment and may result in unfavorable soft-tissue collapse or resorption patterns that complicate implant positioning. This expanded review compares biological, clinical, radiographic, and functional outcomes associated with immediate and delayed implant placement in compromised extraction sites. The discussion integrates long-term survival data, bone remodeling behavior, soft-tissue esthetics, complication profiles, and the role of biomaterials. Emerging trends, such as minimally invasive regenerative protocols and digital workflow integration, are evaluated for their potential to improve predictability in compromised sites . The article highlights that while both methods can achieve success, the choice must be individualized according to defect morphology, systemic considerations, aesthetic expectations, and clinician expertise. Ultimately, both strategies remain viable, but neither is universally superior.