Computerized Provider Order Entry (CPOE) can reduce medication errors; however, its benefits are only achieved when data are entered in a structured format and entries are properly coded. This paper aims to explore the incidence of free-text medication order entries involving hypoglycemic agents in an ambulatory electronic health record (EHR) system with CPOE. Our results showed that free-text order entry continues to be frequent. During 2010, 9.3% of hypoglycemic agents were entered as free-text for 2,091 patients. 17.4% of the entries contained misspellings. The highest proportion of free-text entries were found in urgent care clinics (49.4%) and among registered nurses (31.5%). Additionally, 92 drug-drug interaction alerts were not triggered due to free-text entries. Only 25.9% of the patients had diabetes recorded in their problem list. Solutions will require policy to enforce structured entry, ongoing improvement in user-interface design, improved training for users, and strategies for maintaining a complete medication list.