Writing intensive (WI) courses are well-situated to support students' counterargument skill development, a key element for both academic and civic discourse in today's socio-political environment. However, while many researchers celebrate multi-faceted argumentation, few studies look beyond a dichotomous or "two-sided" approach in post-secondary writing instruction. In this qualitative study, we drew on our established WAC program's extensive WI course proposal system to ask: How do WI instructors describe counterargumentation, both broadly and in relation to their writing assignments? Through grounded theory data analyses, we categorized and qualified instructors' descriptions of counterargumentation use within 350 WI courses and assignments. Although there was agreement on the importance of argumentation, our successive rounds of analysis revealed interesting contradictions in the ways WI instructors conceptualized disciplinary argumentation and how they apprenticed students into argumentative writing tasks. As we explored the tension between instructors' characterization and practice of counterargument, we realized the need to design intentional professional development to help WI instructors teach students how to embrace subjectivity as they design, implement, and assess student writing activities.