In this article, we investigate the role of interactive haptic-enabled tangible robots in supporting the learning of cursive letter writing for children with attention and visuomotor coordination issues. We focus on the two principal aspects of handwriting that are linked to these issues: Visual perception and visuomotor coordination. These aspects respectively enhance two features of letter representation in the learner’s mind in particular, namely the shape (grapheme) and the dynamics (ductus) of the letter, which constitute the central learning goals in our activity. Building upon an initial design tested with 17 healthy children in a preliminary school, we iteratively ported the activity to an occupational therapy context in 2 different therapy centers, in the context of 3 different summer school camps involving a total of 12 children having writing difficulties. The various iterations allowed us to uncover insights about the design of robot-enhanced writing activities for special education, specifically highlighting the importance of ease of modification of the duration of an activity as well as of adaptable frequency, content, flow, and game-play and of providing a range of evaluation test alternatives. Results show that the use of robot-assisted handwriting activities could have a positive impact on the learning of the representation of letters in the context of occupational therapy (V = 1449, p textless 0.001, r=0.42). Results also highlight how the design changes made across the iterations affected the outcomes of the handwriting sessions, such as the evaluation of the performances, monitoring of the performances, and the connectedness of the handwriting.