Electric retrofitting (e-retrofitting) is a viable option for accelerating the renewal of heavy-duty vehicle fleets to reduce the related emissions. We introduce a simulation-based assessment of e-retrofitting strategies for heavy-duty vehicles. Our simulation tool, an electric vehicle fleet simulation toolbox, comprises three modules, namely driving cycles, vehicle dynamics, and vehicle profiles. The first allows for the creation of realistic driving cycles based on GPS data from real routes. The vehicle dynamics and vehicle profiles incorporate, e.g., the modelling of the powertrain and driving conditions. Ten realistic driving cycles were created and used for investigating and comparing three different powertrain alternatives, including the original diesel powertrain, electric with a single-speed transmission and electric with a multi-speed transmission. The vehicles were simulated in two different heavy-load scenarios. First, driving with a cargo load represented by the maximum vehicle weight and second, driving with snow ploughing. We found that the multi-speed transmission in an electric heavy-duty truck significantly improved its traction performance and gradeability. On the other hand, the effect on the electric powertrain efficiency, and thereby on the energy consumption, remained rather minor. Considering the given workload scenarios, our results advocate employing rather than omitting the gearbox in the e-retrofit truck process.