The captain's extended break, taken alongside team-mate Adrien Rabiot, has infuriated Milan supporters and reignited speculation over his future, despite putting pen to paper on a new deal until 2031 back in January.
Maignan and Rabiot were due back at Milanello on 12 August but pushed their return to 16 August, a delay that has coincided with reports of interest from Saudi side Al-Nassr.
The first signs of trouble came on social media, where Maignan quietly deleted photos and removed AC Milan from his bio, echoing behaviour seen from other players before high-profile exits.
According to gazzetta.it, Al-Nassr have made contact over a potential deal for the goalkeeper. Maignan is now expected back at the club's training base on 16 August for a face-to-face conversation with owner Gerry Cardinale and head coach Rúben Amorim.
Time is tight: should Maignan formally request to leave, Milan would need a replacement lined up with barely two weeks left before the transfer window shuts, and reports suggest the goalkeeper had already been ready to leave for Chelsea last summer before being persuaded to stay by Massimiliano Allegri, sporting director Igli Tare and goalkeeping coach Claudio Filippi, all three of whom left the club in May after Milan missed out on Champions League qualification again.
Fikayo Tomori is a separate case but part of the same broader defensive reshuffle at San Siro. The England international was an unused substitute in Milan's recent friendly against Chelsea, a strong signal that his time at the club is drawing to a close.
Tomori will need to be sold this window regardless of Milan's preference, given his contract runs out in 2027 and the club has no intention of losing him for nothing on a free transfer.
According to milannews.it, the previous Milan hierarchy had shaken hands on a contract renewal with Tomori, but Cardinale's overhaul of the club's leadership at the end of May left the defender on the list of players to be moved on. There has been renewed contact with his representatives in recent hours as the club searches for a solution, with Tomori himself said to prefer a return to the Premier League, where he has previously been linked with Newcastle United and other suitors keen to bring him back to England.