The concept of an ‘Operational Claim Point’, (OCP), has recently been proposed as a mechanism for improving the structuring and clarity of Operational Safety Cases. OCPs provide a mechanism by which arguments and evidence in the operational domain can be explicitly connected to design-time risk arguments. This gives rise to a number of benefits: ensuring that system operators are able to focus on just the operational aspects of the safety case relevant to them (hiding irrelevant and potentially confusing design details); making sure that, at the same time, the crucial relationship between the operational safety case and the design-time risk argument is explicitly documented and maintained(helping operators to better understand the safety impact of their work); and allowing design-time safety engineers to specify, in the risk argument, safety claims relating to system operation. We provide worked examples of how OCPs can be used in practice. Through these examples we explore some of the challenges in creating operational safety cases, including the link to the operational Safety Management System. We consider the impact of evidence that becomes apparent during operation, indicating unacceptable risk levels, and argument and evidence that may change depending on the specific choices of different operators of the same system.