Manchester United captain Bruno Fernandes has rejected a second contract offer from the club.
The Portugal midfielder is out of contract at the end of the season, though the club have the option to trigger a 12-month extension until 2028.
United are keen to avoid that eventuality by extending the 32-year-old's existing deal and have been in talks with the Portuguese's representatives in recent months.
But sources have told BBC Sport that Fernandes has rejected the club's second proposal over a new deal at Old Trafford.
Should United fail to agree a fresh deal with Fernandes, it is almost certain that the club will trigger a 12-month extension in his contract before 1 January.
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It is unclear when Fernandes turned down the offer, but it appears unlikely that a resolution is imminent given the upheaval at the club.
Michael Carrick was sacked as head coach on Thursday following the club's worst start to a domestic campaign in 40 years.
USA coach Mauricio Pochettino is expected to replace Carrick, with the Argentine set to be in charge for the first time when United travel to Anfield to face rivals Liverpool on 22 November.
United will be hoping that Pochettino's arrival will persuade Fernandes to commit his future to the club.
Fernandes came close to joining Pochettino's Tottenham in 2019 but a move failed to materialise, with the midfielder signing for United six months later.
The former Sporting midfielder has scored six times in 13 matches for United this season.
Chief football news reporterIn theory, the current contract stand-off between Manchester United and Bruno Fernandes is not a big deal.
It is usual for the first, second and sometimes quite a few more offers to be rejected as part of the rough and tumble of negotiations.
United do have the option to trigger an option to add an extra year. However, there is reason why both sides might be wary to commit beyond that at this stage.
On Fernandes' part, there is a clear desire to compete for the biggest prizes. He can see the best years of his career drifting away. Yet again United have failed to build on a season of promise and he will now be wanting to see what impact Mauricio Pochettino has when he eventually arrives from the United States.
Fernandes was coveted by the Saudi Pro League 18 months ago, although the feeling has been he would prefer to stay in Europe.
On United's side, they will have noted Fernandes' alarming drop-off from the levels he hit last season, when he broke the Premier League assists record and won all the major player of the year honours.
Liverpool committed a huge amount of money to Mohamed Salah's last contract and that turned out to be a heavy financial burden. United will not want to get saddled with a major contract over an extended period for an underperforming player.
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