Dynamic Positioning systems (DP-systems) are becoming increasingly ubiquitous in the maritime domain and is utilized for station keeping in a wide variety of operations, such as drilling and well operations, cargo loading, diving operations, cable and pipe laying. A dedicated Dynamic Positioning Operator (DPO) on the vessel bridge is responsible for controlling this system when it is being used. Accidents and near-misses reports indicate that the sensemaking of DPOs is not always successful. In this paper we investigate the challenges facing such operations from a sensemaking perspective, analysing incident reports and interviewing DPOs to identify areas where improvements could be made to avoid incidents and accidents. Our analysis points in particular to three areas causing challenges: 1) Long periods of “rest” followed by sudden and sometimes unfamiliar shifts in risk-picture that require a fast response, 2) surprising vessel behaviour during certain DP modes, mode transitions and degradations in the DP system, and 3) limited possibility for practicing sensemaking in safety-critical situations, as these situations rarely arise.