Today, patient-specific email messages are being exchanged more frequently among clinicians creating privacy and security concerns within clinics. The purpose of this ongoing project is to determine the usability of a private key infrastructure (PKI) email security system among clinicians at small family practices. The original security intervention involved the clinician's regular machine-based email programs, however, early problems resulted mainly from the lack of standardization among computer systems. A new approach was designed and it involves a web-based security email program. This poster discusses the experiences with both approaches to a PKI system.