Academic advising has been described as the second-most important function in the community college (behind only instruction) toward helping students achieve their goals. Using interview data from 78 students and 33 advisors at one of the nation's largest and most racially diverse community college systems, our qualitative case study examined how academic advisors inform, and directly influence, students' enrollment decisions. Advisors emphasized their role as supporting and scaffolding student decision-making, but not making decisions for students. Most advisors endorsed a developmental approach focused on building students' knowledge and capacity to make better decisions about their own academic trajectory. However, some students had conflicting expectations of the advising relationship (e.g., advisors should tell them exactly what to study, which courses and how many to take), which resulted in frustration and desires for highly prescriptive advising. Advisors recognized a one-size-fits-all advising model would not work well for their diverse student population and rejected prescriptive recommendations, such as uniform advice that each student take 15 credit hours per semester. Instead, advisors considered the totality of each advisee's circumstances (e.g., background, academic preparation, goals, family and work life, transportation) when providing guidance on course load. But determining each student's optimal course load/combination was complicated by the wide range of academic and personal factors advisors had to consider. Consequently, most advisors accentuated the potential risks (for students and themselves) of advising students to attempt too heavy a course load.