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Nail impingement against the anterior femoral cortex during nail insertion, or anterior cortex penetration, has been described in the literature as a worrying complication. We describe a previously unreported surgical failure due to a compromised dynamic distal locking caused by distal jamming of the nail. An 80-year-old male suffered a closed right intertrochanteric femoral fracture. Due to the presence of a long medial fragment, a 240 mm long titanium trochanteric nail was chosen to stabilize the fracture. Dynamic distal locking was performed by placing the distal screw at the inferior rim of the elliptical locking hole to allow compression of the fracture site during weight-bearing. Six-month X-ray follow-up revealed a broken nail and nonunion of the fracture due to failed dynamization of the distal locking screw. The nail was removed and replaced by a total arthroplasty. Due to the femoral anterior bow of the shaft, anterior cortical impingement of the distal tip of a nail may result in the failure of the nail to slide within the diaphyseal canal when using a medium-length nail preventing compression of the fracture. Dynamic distal locking can be ineffective if the ability of the distal nail to slide within the diaphyseal canal is hindered. This type of scenario can represent an opportunity for anterior nail impingement. Distal jamming of the nail can thus compromise dynamic compression at the fracture site during loading, thus inducing nonunion of the fracture, and leading to breakage of the osteosynthesis device. For these reasons, caution is recommended when using medium-length trochanteric nails for unstable trochanteric fractures.