Direct Secure Messaging (DSM) is a sender-initiated communication technology for exchanging patient-specific information among clinicians and disparate healthcare organizations. As DSM adoption increases it becomes more difficult for clinicians and staff to manage the volume and variety of external data received. This can lead to information hazards that can produce cognitive overload and decrease the ability of clinicians to process patient data when reviewing multiple sources. While DSM is one of many options for electronically exchanging health information, we have found that poor user awareness of DSM features and variable EHR capabilities for sending, receiving, and managing messages and their contents demonstrate that additional work is needed to achieve DSM’s potential as a low-barrier, ubiquitous option for clinical interoperability. This paper reviews these problems from end-user perspective and offers best-practices for both senders and recipients of DSM.