Data-art inquiry is an arts-integrated approach to data literacy learning that reflects the multidisciplinary nature of data literacy not often taught in school contexts. By layering critical reflection over conventional data inquiry processes, and by supporting creative expression about data, data-art inquiry can support students' informal inference-making by revealing the role of context in shaping the meaning of data, and encouraging consideration of the personal and social relevance of data. Data-art inquiry additionally creates alternative entry points into data literacy by building on learners' non-STEM interests. Supported by technology, it can provide accessible tools for students to reflect on and communicate about data in ways that can impact broader audiences. However, data-art inquiry instruction faces many barriers to classroom implementation, particularly given the tendency for schools to structure learning with disciplinary silos, and to unequally prioritize mathematics and the arts. To explore the potential of data-art inquiry in classroom contexts, we partnered with arts and mathematics teachers to co-design and implement data-art inquiry units. We implemented the units in four school contexts that differed in terms of the student population served, their curriculum priorities, and their technology infrastructure. We reflect on participant interviews, written reflections, and classroom data, to identify synergies and tensions between data literacy, technology, and the arts. Our findings highlight how contexts of implementation shape the possibilities and limitations for data-art inquiry learning. To take full advantage of the potential for data-art inquiry, curriculum design should account for and build on the opportunities and constraints of classroom contexts.