Henry, who is yet to confirm his future for next year, returned to Fremantle's senior side through last week's loss to Richmond and has held his place in the team for Round 14 - potentially through James Aish's absence rather than form.
But as the season takes its course, the Dockers have looked to steer away from Henry holding his more traditional role as a small forward threat, spending more time in the defensive half as a wide midfield asset.
With Aish's current concussion concerns, Henry could be given the next two games to show his value on the wing under Longmuir.
The Dockers have moved to sew up their forward stocks in the past two weeks alone, handing multi-year deals to veterans Nat Fyfe and Michael Walters and small forward Sam Switkowski, while the Cockburn club is looking to extend the contract of sharpshooter Lachie Schultz following his triggered one-year extension for 2024 following the loss to Richmond.
But despite the recent signing spree, Henry, alongside fringe forward Sam Sturt, has so far been left out of the mid-season retention window that has also seen uncapped defender Karl Worner earn a new deal this week.
Saturday's showing against the Giants will be Henry's 33rd for the Dockers since joining the club as a top 10 selection and just his sixth in 2023. The 21-year-old has worked himself back into the senior side after a dominant month in the WAFL, averaging 23.75 disposals, 4.75 marks, 5.75 tackles and 1.0 goals from his past four matches for Peel.
Fellow members of the 2019 draft class have set their careers on a path to stardom or have already reached that benchmark, with Henry's teammate Caleb Serong likely leading the Doig Medal after 13 rounds while another first-round selection in Hayden Young holds a pivotal role in Longmuir's backline. Both players are penned to Fremantle until the end of 2027 after signing extensions last year.
Top two selections, Matt Rowell and Noah Anderson, are enjoying career-best campaigns, while Kysaiah Pickett and Will Day have proven their value at Melbourne and Hawthorn, respectively, each earning bumper deals that will now take them through to free agency.
The signs have been there for Henry this year, though. His fourth season as a Docker started in style against St Kilda with a career-high haul of 21 disposals - 16 of which were effective - to go along with a pair of goal assists and six score involvements in a low-scoring loss to show glimpses of his ability as a conduit player in the top flight.
His capacity as a running flank option that can accurately move the ball and offer overlap run is where he can be a standout for the Dockers, who have begun to turn toward the future this year with the emergence of second-year locals Matt Johnson and Jye Amiss.
Adding fellow 2021 draftee Neil Erasmus into that mix - a player that would directly rival Henry come selection - the opportunity for Henry to keep his teammate at bay come selection is on offer when Henry faces the Giants on Saturday afternoon.
The Dockers have conceded they may be without Aish for multiple weeks due to his history of head trauma, with the stage set for Henry to demonstrate his ability as a valuable wing option for the club.
With Fremantle looking to return to the winner's column and have the heart of their finals pursuit still beating, this weekend could prove to be a catalyst for Henry's future as a Docker.