Ashley Phillips' proposed switch from Tottenham Hotspur to Middlesbrough has some fresh issues to iron out.
Boro and Spurs have already been business partners this summer, with Will Lankshear joining the Teessiders in a deal worth up to £20million.
Kim Hellberg's side are showing serious transfer ambition this summer, determined to end their decade-long Premier League exile in 2026-27.
Phillips has been strongly linked with a move to Boro this summer, and there was an expectation that he'd be announced over the weekend.
However, that hasn't been the case, and the 21-year-old remains with the Lilywhites for the time being.
Middlesbrough don't wish for that to be the case for much longer though, but the Championship promotion hopefuls have now made a fresh demand to Tottenham.
What sort of deal Middlesbrough may now want for Ashley Phillips
Seemingly not part of Roberto De Zerbi's first-team plans at Tottenham, Phillips could generate another significant cash income if sold this summer.
But, receiving a transfer fee for the England youth international may no longer be the most likely outcome of a deal.
That's because a report from the Daily Mail has claimed that Middlesbrough could now prefer to explore a loan move for Phillips rather than the originally proposed permanent arrangement.
It's stated that Boro would like Tottenham to alter their demands after concerns were raised during his medical with the Smoggies.
Middlesbrough are understood to have agreed an initial £7million fee for Phillips, but the package could've seen the transfer rise to an eventual £20m, the same as Lankshear's.
The report claims that whilst the deal has hit a snag, talks are still taking place between the two parties, and Phillips even spent time at Middlesbrough's Rockliffe Park training complex last week in the hopes of pushing through his transfer.
But why might it be in Tottenham's best interest to try and push Middlesbrough to once again agree to a permanent transfer for Phillips this summer?
Tottenham ready to bank serious profit as Ashley Phillips transfer advances What is Phillips' contract situation at Tottenham?
Despite the fact Phillips has never made a competitive appearance for Tottenham, his transfer stock is as high as it's ever been right now.
Two excellent years on loan with Championship side Stoke City has helped establish himself as a top defender at that level, whilst his age and England youth international pedigree help to make him an even more valuable commodity.
However, his value could start to naturally dip in the near future if Spurs aren't careful, as he's only contracted in N17 until 2028.
As a result of that, should Tottenham not agree to a permanent transfer exit for him this summer, come this time next year and depending on how his 2026-27 campaign goes, getting up to £20m for him may no longer be achievable.
But, even if it means Spurs agree to a slightly smaller initial fee but can keep that maximum potential transfer value in place, then sorting out his sale now may still prove to be the wiser option than a loan.
This would particularly be the case if it was a straight loan to Middlesbrough, or even if it only includes the option to purchase him rather than an obligation.