Health-Related Quality of Life (HRQoL) measurement is a cornerstone of health economics and outcomes research, playing a crucial role in healthcare decision-making and resource allocation. However, accurately capturing and interpreting HRQoL data presents numerous methodological challenges. This podium session brings together four studies that discuss the complexities of HRQoL measurement and utility estimation across diverse contexts and populations. By examining mapping functions, measurement tool comparisons, temporal considerations, and proxy ratings, this session aims to enhance our understanding of HRQoL measurement challenges and inspire innovative approaches to overcome them.