In addition to exploring new methodologies, the workshop will address key challenges such as the explainability and interpretability of decisions, data privacy, and the practical deployment of models using contextual information. While these challenges are well-recognized in the ML community, particularly with the rise of large language models, they remain underexplored in the Operations Research community. By fostering collaboration and knowledge exchange, the workshop aims to develop scalable models, promote better benchmarking practices, and expand the applicability of contextual optimization to a wider range of real-world problems.