This qualitative, multiple site case study addressed five key areas (a) accountability; (b) student affairs assessment; (c) student affairs strategic planning; (d) student learning in student affairs; and (e) linkages: connectivity of assessment, strategic planning, and student learning. The study drew upon semi-structured, Skype-based interviews from student affairs practitioners at institutions in six accrediting regions and by analyzing related documents. Research questions framing the study were 1) How are divisional assessment processes linked to student learning? 2) How are divisional strategic plan(s) linked to student learning? 3) How do student affairs divisions integrate or link strategic planning and assessment? 4) Who is involved in divisions’ assessment and/or strategic planning, and what are the major responsibilities of these individuals? 5) What are common practices of divisions that successfully link assessment, strategic planning, and student learning? Findings are illustrated across case themes and patterns and organized according to their relationship to assessment, strategic planning and student learning. Implications of this study illustrate the need to increasingly professionalize student affairs work through credentialing so that more practitioners are familiar with scholarly research and can build instruments to understand how student affairs contributes to learning. Study implications also show that professional associations and accrediting agencies can work to set techniques and outcomes that clearly demarcate student learning or, at best, the intention thereof within strategic plans and assessment documents. Lastly, the study results suggest connection of divisional funding models to drive desired outcomes of connections between assessment, strategic planning, and student learning.