Purpose: Patients undergoing liver transplantation (LT) are routinely assessed for surgical difficulty, but the predictability of these assessments is unreliable and yet unquantified. We aimed to identify and quantify risk factors for surgical complexity in LT. Methodology: Retrospective review was performed of all adult liver transplants performed at a single centre between 2012 and 2023. Surgical difficulty was defined by three surrogate variables; operating time, estimated blood loss, and intraoperative complications. Patients were allocated points based on their percentiles for each surrogate and subsequently grouped into low (LR), intermediate (IR) and high or very high (HR) risk cohorts. Cohorts were compared based on demographic, biochemical, surgical and radiological data. Chi-square and ANOVA tests were used and odds ratios (OR) calculated with p-values <0.05 considered statistically significant. Results: A total of 771 patients were included in the study (LR; n=225, IR; n=346, HR; n=200). Patients in the HR cohort were associated with significantly longer hospital stay (HR;36, IR;12, LR;13 days, p<0.01) and Clavien-Dindo III complications (HR;33.5%, IR;16.5%, LR;12%, p<0.01). Factors contributing to surgical difficulty were re-transplantation (OR 6.48, p<0.01), portal venous thrombosis (OR 5.45, p<0.01), spontaneous bacterial peritonitis (OR 3.61, p<0.01), prior hepatobiliary surgery (OR 2.95, p<0.01) and prior open abdominal surgery (OR 2.95, p<0.01) Conclusions: We identified five key factors associated with significant risk for surgical complexity in LT. These findings highlight the importance of identifying these factors pre-operatively and planning perioperative resources accordingly to optimise outcomes.