In "Teaching Against the Grain: Critical Assessment in the Library Classroom," Maria Accardi sought a critical, feminist approach to assessment that questioned power structures, celebrated learners, and found strength in diverse perspectives and voices. This article expands on Accardi's work to explore a care-based assessment framework rooted in the foundations of critical assessment, relational-cultural theory, and critical generosity. This includes a critique of the current language of assessment in library and information science literature and higher education; an examination of models for more caring versions of assessment (particularly those from other feminized professions); and a reframing of the conversation around assessment from one of demonstrating value to one of embodying a value of care and connection in learning for both students and librarians.