Medication reconciliation is a systematic and comprehensive review of medication regimens during care transitions aiming to prevent adverse drug events. Poorly executed transitions negatively impact patient welfare and cause financial burden. Medication-related problems (MRPs) experienced during transitions to an assisted living facility (ALF) were evaluated. Data was collected from pharmacy records for transitions to an ALF over three months, including demographics, medications, potentially inappropriate medications, and MRPs. MRPs were categorized and summarized using descriptive statistics. Forty-five patients (71% female) experienced 59 transitions. Average age was 85.6 years. Median length of stay away from the ALF was three days. There were averages of 18.3 pre-transition medications, 12.5 medications in the discharge orders and/or upon ALF admission, and 15.9 final medications. 979 MRPs were identified, mostly no indication documented, followed by underuse, overuse, and non-adherence. Many of the identified MRPs are potentially preventable. Interventions are needed to reduce MRPs during ALF transitions.