Assessment of swimming and survival skills is a crucial part of any swimming and lifesaving programme. Unfortunately, quite often, it is also the weakest part of the programme itself. Inadequate skills assessment and verification might lead to ineffective skills acquisition and development, to a false sense of safety and over confidence in the water that can be extremely dangerous. Assessor experience and observation skills, assessment methodology, and criteria are all closely inter-linked and their interaction will somehow determine the assessment outcomes. Our paper analyses some of the current issues in these areas of the assessment process, such as assessor’s lack of theoretical knowledge and experience, criteria not fit for purpose, and methodological constraints. As examples for our discussion and to highlight these issues, we used two very important core aquatic skills, which are also fundamental survival skills: sculling and eggbeater kick. We also stressed the importance of having a sound understanding of the principles of movement in the water as a corrective capability. Finally, based on motor learning and motor development studies, we proposed an assessment process that focuses more on the observation of performance improvement, consistency or stability, persistence, level of effort, attention, and adaptability.