The paper presents the potential benefits and conflicts of the encounter between Jewish ultra-orthodox (UO) children - belonging to a closed and segregated group - and art therapy - with its cultural, Western, secular, and professional characteristics. The paper describes the complex interface between the therapeutic use of art as a form of free expression and religious commandments and restrictions. The dialogue between art, therapy, and cultural religious boundaries is described through a case study of an 8-year-old UO boy and a secular female art therapist. Issues such as self-expression, gender roles, and identity exploration are discussed, emphasizing the unique characteristics, benefits, and conflicts of such an encounter.