Objectives: Insertion of rigid uniplane bent femoral nails through the piriform fossa has been reported to cause neurovascular complications. New nails were designed for more lateral entry points. However, these may be associated with a higher risk of iatrogenic fractures. This study investigated if two differently bent nails with more lateral entry points induce higher cortical bone strains than a uniplane bent nail introduced through the piriform fossa. Methods: Three groups of 8 cadaveric femurs were instrumented using the following nail systems and entry points: Cannulated Femoral Nail, piriform fossa; Antegrade Femoral Nail, trochanteric tip; and helical nail, lateral of the trochanteric tip. During insertion, the maximum principal bone strains were recorded at 9 locations at the proximal femur and the diaphysis. The occurrence of iatrogenic fractures or fissures was documented. Results: The highest strains recorded were between 2000 and 4500 µm/m and mainly located at the posterior aspect of the greater trochanter and at the medial side of the entry point. In most of these cases fissures or fractures occurred, the number of which was higher for the trochanteric tip group as compared with the other groups. This was thought to be due to the thin cortical walls as a result of the larger reamer diameter in this group. Low strains (below 2000 µm/m) occurred at the medial cortex where the laterally inserted nails were expected to impinge. Conclusions: Bone strains at the medial impingement location were low for all nails. Entry portals with thin cortical walls due to, for example, larger reamer diameters and a small greater trochanter seem to be more susceptible to insertion accuracy, which may influence strain and fissure or fracture occurrence. Furthermore, we do not recommend determination of the entry point of laterally inserted nails based solely on anatomic landmarks of the greater trochanter because this may influence insertion accuracy. This implies that biplanar imaging is important for accurate and safe insertion of laterally started nails.