Spotify gets a Wrapped; your media server deserves one too. Rewindarr is an open-source companion for Plex and Jellyfin that turns play history into a story your users step through, card by card: total watch time, how it split across movies, shows, and music, how they rank against the average viewer, and the viewing personality their habits earn them, ending in a summary they can save as an image and share. The same deployment doubles as an everyday dashboard for the whole server, with watch time, requests, library size, and per-library leaderboards for movies, shows, music, and users across a week, a month, a year, or all time. Live activity shows what is streaming right now, and searchable history groups binges together so a weekend disappears into one tidy entry. Ratings from TMDB, IMDb, and Rotten Tomatoes sit beside every title, request buttons reconnect viewers with deleted favourites through Seerr, and anonymisation trims user details when you share the dashboard wider. Statistics flow in from Tautulli or Tracearr for Plex and from Tracearr for Jellyfin, everyone signs in with the Plex or Jellyfin account they already have, and the installable app works on the TV-side phone as happily as on a desktop. Running on a dedicated VPS on RepoCloud with guaranteed CPU, RAM, and SSD, full root SSH access, and a browser serial console. GPL-3.0 licensed.