Jesse Lingard's future hangs in the balance with Newcastle refusing to meet Manchester United 's demand over a contentious survival bonus.
The attacking midfielder, 29, has just over four days remaining to secure the move away from Old Trafford he seeks before the January transfer window slams shut.
Newcastle are in pole position for Lingard's services as the Red Devils will not allow him to depart for Tottenham or West Ham, his other suitors, because they are viewed as rivals for a top-four finish in the Premier League.
But the Magpies are still some distance from striking a deal to sign Lingard on loan for the remainder of the season.
Manchester United have set out three requirements which must be met before the England international can leave - and one is proving to be a sticking point.
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They are demanding Newcastle - who are 18th in the table - pay a huge bonus of £12million if Lingard joins and helps them avoid relegation to the Championship with his performances during the run-in.
On top of that, Eddie Howe's side must cover the player's £100,000-per-week wages and pay a loan fee in the region of £6million to get the deal over the line.
Lingard is out of contract at the end of the season, so it is understandable Manchester United want to earn as much as possible from any transfer.
As Premier League survival is valued at around £100million, a £12million sum to be paid if Newcastle avoid the drop may not be as exorbitant as it first appears.
Indeed, the Tyneside club's hopes of survival would be boosted dramatically if they secured Lingard's services for their 17 remaining games.
He had a brief but blistering stint with West Ham during the second half of last season, scoring nine goals and assisting five times in 16 appearances for the Irons.
However, questions are being raised of whether it is reasonable for the Red Devils to demand such a large fee for a player who will leave for free in the summer.
Indeed, Newcastle will need to pay roughly £20million to meet all the requirements, which is far more than Lingard is worth with a matter of months left on his contract.
This leaves the player's future unclear and both clubs at a crossroads, with some sort of compromise the only solution for the deal to progress.
Lingard's anger at being denied the exit he craves may only grow as he looks on at the relative ease with which teammate Donny van de Beek could leave.
The Dutchman, previously a target for Newcastle, is heavily linked with Crystal Palace but, like in Lingard's case, time is running out for the loan to materialise.
