Although trochanteric fractures (TF) are a frequent event in the geriatric population, studies reporting on complication rates associated with surgical treatment are sparse. Thus, this study investigated the relevance of fracture-, implant-, and surgery-associated complications in TF. Furthermore, the role of possible risk factors for the before mentioned complications was investigated. A consecutive series of patients with TF treated by intramedullary nailing with a sliding screw device was evaluated. Data were sampled retrospectively from the hospital patient information system and anonymized at the source. Demographic data and information regarding fracture pattern, the treatment performed, hospital stay, and evaluation of operative and follow-up radiographs were analyzed. Intraoperative problems (i.e., technical problems with the implant, intraoperative fracture) and postoperative complications were investigated. Postoperative surgical complications were noted in 11.7%. The most frequent surgical problem was a difficult fracture reduction (13%) and intraoperative fracture dislocation (3.6%). The most frequent postoperative complication was intra-hospital mortality (3.6%), delayed/non-union (2.7%), and a cut-out of the lag screw in the femoral head (2.3%). Implant failure (1,4%) was significantly associated with morbid obesity while cut-out (2,3%) correlated with a higher tip-apex distance (TAD). A complex fracture type and a suboptimal screw position significantly increased the cut-out rate to 5% (p = 0.018). Complications after TF treatment occur frequently. While patient-associated variables such as morbid obesity cannot be influenced by the surgeon, correct fracture reduction and implant positioning remain to be of highest importance.