In late 2016, the Special Collections & University Archives (SCUA) at GVSU LIbraries were approached by a faculty member with a request to help retrieve a series of important emails, journals, and film production notes that were stored electronically on two very old (legacy) Macintosh computers. This presentation was used to provide the Mid-Michigan Digital Practitioners community with an overview of the materials and the use case being presented. Attention was drawn to the challenges of connecting and retrieving data from obsolete computer technology and feedback was solicited for strategies and best practices to follow.