This naturalistic multiple-case study design (N = 6) examined the clinical use of a modified Draw A Story assessment as a therapeutic tool for a hospice art therapy program. The aim was to recontextualize a standardized art-based assessment for use as a creative art-based tool. Client participants were video recorded while creating a Draw A Story drawing, followed by viewing an edited version of the video to stimulate responses that tested clinical assumptions, including projection, prestructured materials, and flow. Results indicated that participants utilized the modified Draw A Story to engage in a satisfying creative process with elements of a flow experience. The modified Draw A Story might be effective as an extension of the expressive function for art therapy.