The Disconnected Projects
An Easter egg in Obi-Wan Kenobi that is incredibly well hidden actually connects to Star Wars: The Rise of Skywalker in the most hilarious of ways. When concerning the Star Wars franchise, Obi-Wan Kenobi and The Rise of Skywalker are two of the more disconnected projects.
An overhead shot of a Tri-Wing ship from Star Wars
The Rise of Skywalker is the last Star Wars movie in order of chronology, though this is expected to change via Rey Skywalker's New Jedi Order story. Regardless, The Rise of Skywalker and Obi-Wan Kenobi are separated by over 40 years in the Star Wars timeline.
As such, any Easter eggs between the two projects are highly unlikely. Perhaps the most overt connection between the two is Ewan McGregor's voice cameo in The Rise of Skywalker as Obi-Wan Kenobi, willing Rey to stand and fight against Palpatine. However, one of the more understated Easter eggs found in Obi-Wan Kenobi that links to The Rise of Skywalker is hilarious, if only for the strange nature in which it was originally conceived.
The Creation of the Tri-Wing
The final Skywalker Saga film included the most unlikely alliance between Lucasfilm and the iconic automobile manufacturer.
The hilarious conception in question comes from Lucasfilm and Porsche, with the two companies collaborating to create a new starfighter for Star Wars: The Rise of Skywalker. The starfighter in question is named the Tri-Wing - its full title being the Tri-Wing S-91x Pegasus Starfighter - and was a ship designed by those at Porsche alongside the concept designers at Lucasfilm. The intention of the collaboration was to create a starfighter that looked as though it could exist in both the real world and the fantastical galaxy of Star Wars.
This design was naturally conceived for promotional benefits. The Tri-Wing was first unveiled shortly before the premiere of Star Wars: The Rise of Skywalker, looking to capitalize on the boost in promotion that both Lucasfilm and Porsche would receive from the mutually beneficial collaboration. However, this was not simply a marketing gimmick as evidenced by the connection between Star Wars: The Rise of Skywalker and Obi-Wan Kenobi brought about by the Porsche-Lucasfilm design.
The Easter Egg in Obi-Wan Kenobi
The connection between the two disparate Star Wars projects is found in Obi-Wan Kenobi episode 1. In the first episode of the Disney+ show, audiences are introduced to a young version of Princess Leia. The character's first scene shows her abandoning her royal duties to play in the woods of Alderaan with her droid Lola. Leia is shown sitting in a tree, wistfully gazing at starships leaving the planet's port and making up stories and scenarios for each one.
Young Leia smiling next to a shot of a Tri-Wing in Obi-Wan Kenobi
After spotting a handful of freighters that do not muster any excitement in the princess, Leia remarks: 'Ooh, a Tri-Wing. That's a new one.' This is accompanied by a shot of a Tri-Wing flying away from Alderaan. This Easter egg builds on the creation of the ship for The Rise of Skywalker in a suitably meta way, with Leia even describing the ship as new given its development in real-time only came three years before Obi-Wan Kenobi's premiere. Usually, this kind of Easter egg would be little more than a reference to an iconic Star Wars ship, but the unusual nature of the Tri-Wing’s conception makes it much more humorous.
The Future of the Tri-Wing
Given the ship's appearance in Obi-Wan Kenobi, the question is raised over whether the Star Wars franchise will ever utilize the Tri-Wing's design again in the future.
NewRepublicInsignia
As it turns out, there is a way that the franchise could bring back the Tri-Wing in a way that both honors the ship's creation and works within the context of the Star Wars timeline. Regarding the Star Wars timeline, the Tri-Wing's only mention before Return of the Jedi comes in the aforementioned scene in Obi-Wan Kenobi.
Din Djarin in front of the Living Waters in The Mandalorian season 3.
Canonically though, the Tri-Wing was created to be a vessel for the New Republic. The original design of the ship stated that it was not part of the Rebel Alliance fleet, instead being used more prominently after Return of the Jedi and the formation of the New Republic. As such, this hints that the Tri-Wing could very feasibly be used again going forward as a large portion of Star Wars' recent TV efforts like The Mandalorian and Ahsoka have been set in the New Republic section of the timeline. As a result, Obi-Wan Kenobi’s Easter egg to The Rise of Skywalker may not be the last of the Tri-Wing starfighter.
Ahsoka With Tales of the Jedi Poster