The HIV care continuum illustrates steps needed to reach HIV viral suppression, including retention in care. The continuum's retention measure does not account for gaps or reengagement in care and thus provides an incomplete picture of long-term engagement. We used a claims database to determine the proportion of privately insured persons with HIV who experienced a gap in care and subsequently reengaged between 2008 and 2012. A gap was defined as no office visit claim in >6 months and reengagement as ≥1 office visit claim after a gap. Cox proportional hazards models were conducted to determine factors associated with time to first gap and time to reengagement. Of 5142 persons in the study, 79% were males and median age was 46 years (range, 19-64 years). No race/ethnicity data were available. Thirty percent (n = 1555) experienced a gap. Median time to first gap was 15 months (IQR: 6-30). Median gap length was 3.2 months. Seventy percent with a gap reengaged; 22% reengaged more than once. Of 1086 patients who reengaged, 224 (21%) eventually had a terminal gap. Residence in the North Central region (HR 0.73, 95% CI 0.62-0.87) and having ≥1 Charlson comorbidities (HR 0.85, 95% CI 0.73-0.99) were associated with shorter time to reengagement. The majority who experienced a gap reengaged within a relatively short period and remained in the cohort at 60 months. However, 21% of those reengaging had a terminal gap by 60 months, which should alert providers to the eventual potential for loss to follow-up. The analysis was limited by inability to distinguish between HIV-specific and non-HIV-specific care visits.