Over the coming months and years, the discoverability of communications made through real-time chat software such as Slack and ephemeral messaging applications such as Signal will continue to come into focus. The COVID-19 pandemic has accelerated the corporate adoption of these applications as they promote the efficient exchange of information. While the use of ephemeral messaging applications in particular stands to potentially alter the traditional framework through which courts examine what electronically stored information (ESI) is discoverable, and what steps a party must take to satisfy their obligations under the Federal Rules of Civil Procedure and its state analogues, the Federal Rules provide a helpful framework for companies to follow when determining their retention obligations both in and out of the litigation context. While ephemeral messaging is, strictly speaking, anathema to the duty to retain documents once litigation is reasonably foreseeable (separate and apart from statutory or other obligations), courts and counsel must anticipate how these cutting edge communications platforms interact with an entity's discovery responsibilities, while simultaneously recognizing the functionality of ephemeral messaging for organizational communication and data footprint reduction.