A system enabling smart versioning of files is provided. Techniques disclosed herein enable a system to snap to new versions of a file based on one or more measures of user interactions with the file. For instance, a system can create a new version number for a file based on an amount of time a user has spent editing the file, a number of saves that have occurred, and/or a quantity of data applied to edits of the file. The techniques disclosed herein can also utilize telemetry data to fine tune weightings that are applied to data measuring specific types user activity to provide results that best serve a range of use scenarios and file types. By providing version numbers of a file that are based on user interactions, a system can provide more meaningful version numbers that are aligned with the contents of a file.