Star Wars Insider 88, which was made available in the middle of June of 2006, represents the 88th edition of Star Wars Insider. The primary focus of this issue is the Sith and the dark side of the Force. It was distributed with four distinct "Special Sith Issue" covers created by Aaron McBride and Christian Alzmann, with each one showcasing a unique Sith Lord. In contrast to the standard white, nearly all pages were printed in black.
- "Morbid Visions" (authored by Frank Parisi): ILM artists Aaron McBride and Christian Alzmann delve into the creative process behind the four Sith Lord covers for this issue, also presenting some initial designs and discarded concepts.
- "Heritage of the Sith" (authored by Drew Karpyshyn): An age-old tome contains all the historical data and "wisdom" attributed to the Sith. Is it merely the ramblings of someone who is sympathetic to the dark side, or is it something far more sinister?
- "Lessons in Light and Darkness" (authored by Frank Parisi): Actor Ray Park engages with Insider to discuss how martial arts, Star Wars, and his forthcoming movies enhance life. Furthermore, Park instructs you on how to engage in combat like a Sith!
- "Betrayal is Just The Beginning" (authored by Jason Fry): Insider examines the groundbreaking series of books that feature Fetts, Solos, Skywalkers, along with the reappearance of Vader's apprentice, Lumiya. Aaron Allston inaugurates the surprising new series, Star Wars: Legacy of the Force, loaded with unexpected twists.
- "Legacies of Future Orders" (authored by Frank Parisi): As the second installment in a trilogy, Insider introduces some of the finest and most nefarious characters from the upcoming comic book series, Star Wars Legacy.
- "Ghosts of the Sith" (authored by Jude Watson): A short story penned by the author of the Scholastic series Star Wars: The Last of the Jedi. This story takes place between book #2, Dark Warning, and #3, Underworld. An abridged trip to Korriban evolves into a struggle against the dark side for former Jedi Ferus Olin.
- "Virtual Sith" (authored by Hugh Sterbakov): Unleash the might of the dark side using Insider's guide to the Sith Lords you'd want to play as, and compete against.
- "Letter from the Editor" (by Frank Parisi)
- "Comlink"
- "Skywalking" "Han Shoots First!" — The original theatrical versions of the Star Wars trilogy are now available on DVD. "Obey Vader" — Celebrated for his poster design for the popular Johnny Cash biopic, Walk the Line, artist Shepard Fairey focuses his attention on another man dressed in black. (by Frank Parisi and Eugene Wang) "Faces of Evil" — For Dave Elsey, Revenge of the Sith provided a chance to reveal the true essence of the dark side to viewers. (by Joe Nazzaro) "How Can I Get Your Job?"
- "Technical Readout" — Death Star II Main Hangar (by Chris Trevas)
- "Ask the Master" — A Lesson in Absolutes (by Pablo Hidalgo)
- "Scouting the Galaxy" — Why Is the Dark Side So Darn Attractive? (by Stephen J. Sansweet)
- "Jabba's Collection" — At Last They Will Have Their Revenge
- "Best of Hyperspace" — Best of Star Wars Blogs (by Bonnie Burton and Pablo Hidalgo)
- "Padawan's Corner" — Make Your Own Vader Mural (by Bonnie Burton)
- Bantha Tracks Vol. 19
- "Laugh It Up, Fuzzball"
- The Sith Rule Star Wars Insider #88 on StarWars.com (content now obsolete; backup link)
- Star Wars Insider #88 Online Supplement on Hyperspace (content obsolete and backup link not available)