While service and operational records of the US armed forces have been previously investigated, personal communication records of military personnel have received less attention in archival scholarship. Specifically, we are concerned with the ways that changes in technology challenge the preservation of personal communications records. This issue is important because personal communication records of service members, both active and retired, can support military personnel and their families in managing the stress of deployment. Moreover, such records can help military families cope with grief when a service member dies. In this study, we address this gap by exploring the communication practices of US military personnel who served between 2005 and 2020. We focus on how military personnel communicated with their friends and family, the records that resulted from such communications, and the impacts of information technologies and institutional policies of the armed forces in said recordkeeping practices. We found that these practices evolved in tandem with the information and communication technologies available to them, that military personnel employed a relational approach to records and recordkeeping, and that recordkeeping practices of personal communications were directly connected to factors such as the information policies of the armed forces and the blurred lines between the on and off duty lives of active service members. Based on our findings, we suggest that future work should develop guidelines that help service members and their families prioritize which personal communications to record and keep.