The ever-changing needs of the labor market, driven in particular by the rapid development of information technologies, also require employees to continuously upgrade their skills and knowledge. This has highlighted the need to adapt tertiary education to make it more flexible and responsive to labor market needs, which is also one of the highlights of the European Union’s (EU’s) Recovery and Resilience Plan (RRP). Under this plan, various pilot projects are funded, and we focus on the findings of the pilot project that offers shorter study programs under the topic “Advanced Computer Skills.” Such shorter study programs also face similar challenges as full-time study programs. Using the data gathered by the implementation of three surveys, i.e., the survey among the learners, the survey among the education providers, and the final survey among the learners, after the end of their short study program, we have observed that motivation, lack of prior knowledge, and lack of time management skills are at the forefront among learners, while dropouts and questions about the introduction of compulsory attendance and hybrid delivery model are at the top of the list among education providers. We conclude the chapter by discussing how to address these challenges and also offer solutions that will have wider applicability, particularly in the case of full-time study programs.