Background/Objectives: Low-density cancellous bone can amplify crestal cortical strain around implants because trabecular support is reduced. Osseodensification (OD) compacts trabecular bone and may create a peri-osteotomy densified zone, but its strain-level effects in osteoporotic-like bone are unclear. Given that osteoporosis/osteopenia in aging populations reduce trabecular support and can increase crestal cortical loading, this study tested whether an OD-inspired peri-implant densified trabecular zone lowers high-tail crestal cortical strains versus conventional drilling in an osteoporotic-like cancellous model. Materials and Methods: A 3D finite element mandibular posterior segment (2.0-mm cortical shell and D4 cancellous core) was modeled with a 4.3×11.4-mm titanium implant and a cemented monolithic zirconia crown. CD used a 4.0-mm osteotomy in D4 bone. OD used the same osteotomy plus an axially varying concentric densified shell (D1→D3 radially) with minor buccolingual cortical expansion. The implant–bone interface was bonded. Static 100 N loads were applied axially and obliquely (45°). Outcomes were εeq, εmax, and εmin, summarized as mean top-10 nodal values. Results: OD reduced crestal cortical strains under both loads. Axial loading: εeq 1470→1210 µε (−17.7%), εmax 1420→1150 µε (−19.0%), |εmin| 900→683 µε (−24.1%). Oblique loading: εeq 3370→3040 µε (−9.8%), εmax 2510→2310 µε (−8.0%), |εmin| 3040→2770 µε (−8.9%). Oblique loading produced higher cortical strains than axial loading in both models. Conclusions: OD-inspired peri-implant densification attenuated high-tail crestal cortical strain demand in this osteoporotic-like model, whereas off-axis loading remained the dominant driver of elevated strain. These findings support occlusal/prosthetic strategies that minimize oblique forces and warrant experimental and clinical validation.