Technologies for computing context replay include a computing device having a persistent memory and a volatile memory. The computing device creates multiple snapshots that are each indicative of a user's computing context at a corresponding sync point. The snapshots may include metadata created in response to system events, memory snapshots stored in a virtual machine, and/or video data corresponding to the computing context. At least a part of the snapshots are stored in the persistent memory. The computing device presents a timeline user interface based on the snapshots. The timeline includes multiple elements that are associated with corresponding sync points. The timeline elements may visually indicate a salience value that has been determined for each corresponding sync point. In response to a user selection of a sync point, the computing device activates a computing context corresponding to the snapshot for the selected sync point. Other embodiments are described and claimed.