ABSTRACT Community college counselors play an important role in supporting students’ decision-making as they navigate toward varied academic goals. Most community college students intend to transfer and thus must navigate the regulations and policies of two institutions, and many follow nonlinear enrollment patterns. Knowledgeable, personalized advising is an important resource for students in community colleges. Yet, counselors often juggle multiple roles, manage large counselor-to-student caseloads with limited resources, and must understand and meet the needs of a growing diverse student body. This study examines the factors that affect community college counselors’ ability to assist community college students in navigating multiple institutions at once while taking classes at a four-year university through a policy called cross-enrollment. To do so, we employed focus group interviews with 29 community college counselors from three community colleges in California. We found that institutional resources and support, cross-campus collaborations, counselors’ perception of the benefits and challenges associated with cross-enrollment, and counselors’ perception of the ideal cross-enrollment student were factors that affected counselors’ ability and willingness to facilitate cross-enrollment efforts. The findings suggest that improving the uptake of cross-enrolling is contingent on institutions improving their cross-institutional collaborations and providing community college counselors with adequate professional development and resources on the policy.