Selecting a health plan in a health insurance exchange is a critical decision, yet consumers are known to face challenges with health plan choice. We surveyed new enrollees in two state-based exchanges in 2015 to investigate how a nonelderly, primarily low-income population chose their health plans and the implications of shopping behavior for early experiences in their plans. Financial considerations were most important to enrollees. Prior Medicaid enrollees and the uninsured were more likely to have multiple shopping challenges (e.g., difficulty identifying the best or most affordable plan, fair/poor experience, unmet need for help) than enrollees with prior employer coverage (42.9% vs. 32.5% vs. 16.4%, respectively, p < .01). Shopping challenges were associated with difficulty finding a doctor, understanding coverage, and getting questions answered. Assistance targeting enrollees who previously had Medicaid or lacked insurance could improve both shopping experiences and downstream outcomes in plans.