Losing a bottom hole assembly (BHA) is one of the most costly unplanned drilling events that can occur for an operator. Time spent fishing for the lost assembly, the rig time wasted waiting on the mobilization of equipment and people, as well as the additional costs of whipstocks, cement, and directional tools significantly increase the cost of a well and often results in exceeding the approval for expenditure (AFE). The new well plan may also lead to any number of problems with tortuosity and torqueand-drag farther down the wellbore. Typically, these expenses are invoiced individually, obscuring the cumulative cost to reach the same true vertical depth (TVD) as the stuck assembly. This paper will analyze data and case studies in the Gulf of Mexico (GOM) to perform a risk analysis that includes the true cost of sidetracking a well, with and without additional LWD technology in the drill string providing key real-time measurements.