The exhaust gas in an internal combustion engine provides favorable conditions for a waste-heat recovery (WHR) system. The highest potential is achieved by the Rankine cycle as a heat recovery technology. There are only few experimental studies that investigate full-scale systems using water-based working fluids and their effects on the performance and operation of a Rankine cycle heat recovery system. This paper discusses experimental results and practical challenges with a WHR system when utilizing heat from the exhaust gas recirculation system of a truck engine. The results showed that the boiler’s pinch point necessitated trade-offs between maintaining adequate boiling pressure while achieving acceptable cooling of the EGR and superheating of the water. The expander used in the system had a geometric compression ratio of 21 together with a steam outlet timing that caused high re-compression. Inlet pressures of up to 30 bar were therefore required for a stable expander power output. Such high pressures increased the pump power, and reduced the EGR cooling in the boiler because of pinch-point effects. Simulations indicated that reducing the expander’s compression ratio from 21 to 13 would allow 30% lower steam supply pressures without adversely affecting the expander’s power output.