This art-based collaborative research study explored the perceptions of four group art therapists who engaged in the practice of creating art alongside their clients. It aimed to explore the challenges these art therapists perceive to be associated with their practice of in-session artmaking through a series of in-depth interviews incorporating discussion and artmaking. Analysis included coding of interview transcripts, reviewing art, and isolating video and audio clips which were first organized into video summations and then refined into a culminating video. Outcomes included three contemporary risks associated with creating alongside clients and four skills therapists in this study developed to mitigate these challenges: (a) multitasking, (b) shifting awareness, (c) letting go of control, and (d) media awareness. The study provides a practical discussion of how experienced art therapists apply this practice and suggests skills that may be needed to successfully manage potential challenges. It also adds the term “companioning artmaking” to the literature. This inclusive term describes the practice of creating art in the presence of group members to be with and beside them while acting as a role model and companion.