The ethics of AI as both material and medium for interaction remains in murky waters within the context of musical and artistic practice. The interdisciplinarity of the field is revealing matters of concern and care, which necessitate interdisciplinary methodologies for evaluation to trouble and critique the inheritance of "residue-laden" AI-tools in musical applications. Seeking to unsettle these murky waters, this paper critically examines the example of Holly+, a deep neural network that generates raw audio in the likeness of its creator Holly Herndon. Drawing from theoretical concerns and considerations from speculative feminism and care ethics, we care-fully trouble the structures, frameworks and assumptions that oscillate within and around Holly+. We contribute with several considerations and contemplate future directions for integrating speculative feminism and care into musical-AI agent and system design, derived from our critical feminist examination.