The England international has made five appearances and played 210 minutes so far this season, starting three matches, but has struggled to establish regularity and make a significant impact.
Loftus-Cheek has also been used in a more advanced role, where his physical qualities and ability to make late runs can be utilised. However, his performances have not yet made him a central figure in the new project under Ruben Amorim.
His workload has also attracted attention. According to Lega Serie A statistics, Loftus-Cheek has covered 25.8 kilometres across his first five league appearances, the lowest total among AC Milan players with five appearances and even below goalkeeper Mike Maignan.
The situation has inevitably raised questions about his future, particularly because Loftus-Cheek was initially included on the list of players who could leave before subsequently being brought back into the squad.
His contract expires in June and the first discussions over a renewal took place during the summer with Stellar, the agency representing the midfielder.
Those talks have now stalled.
Loftus-Cheek currently earns around €4 million net per season and Milan are understood to want to assess his performances before deciding whether to offer him a new contract.
The next few months could therefore determine whether the 1996-born midfielder remains part of the club’s plans beyond the current campaign.
For Loftus-Cheek, the immediate objective is to increase his influence on matches and convince Amorim that he should remain an important part of the project.
A stronger run of performances could change the situation, while continued uncertainty could leave Milan facing the possibility of losing him as a free agent when his contract expires.
There is already potential interest elsewhere, with clubs in the Premier League monitoring the situation and able to pursue the midfielder without paying a transfer fee if he reaches the end of his Milan contract.
Loftus-Cheek joined Milan after spending his formative years at Chelsea and has already experienced football at the highest level in England.
A return to the Premier League would therefore represent a possible next step if the current situation at Milan does not change.
For now, however, the midfielder remains under contract and the decision will depend largely on his performances during the coming months.
Milan have not closed the door on a renewal, but the existing discussions are frozen while the club assesses his contribution.
The remainder of the season will therefore be important for Loftus-Cheek as he attempts to establish greater continuity and influence under Amorim.