Background: People with intellectual disabilities in Flanders (Belgium) often rely on their direct support professionals (DSPs) to engage in meaningful activities. While structured approaches exist to guide engagement, limited insight is available into the specific support DSPs need in practice. Methods: A descriptive qualitative study was conducted using in-depth interviews with 13 DSPs. Thematic analysis was performed using NVivo 12. Results: Five themes emerged: (1) Basic assumptions regarding meaningful activities, (2) Relationship between people with intellectual disabilities and DSPs as a prerequisite for enabling meaningful activities, (3) Facilitating factors in enabling meaningful activities, (4) Areas of tension in enabling meaningful activities, and (5) Barriers to enabling meaningful activities. Conclusions: DSPs recognise the importance of meaningful activities but face significant challenges in practice. Addressing these challenges requires training and support tailored to their specific needs and the realities of their daily work, ensuring they are better equipped to foster engagement in meaningful activities.