Liverpool have failed to make any real progress in talks with midfielder Jordan Henderson over a new contract, with the door now tentatively opened to a potential exit from the club.
The Reds have been looking at their contract situation this summer and have already started working on some extensions. Goalkeeper Alisson is set to sign a new deal, as is Fabinho, and talks with Henderson have been rumbling on for a few weeks now.
However, despite some early optimism, The Athletic note that negotiations with the 31-year-old have slowed down drastically, creating significant uncertainty over whether the club captain will actually stay at Anfield to see out the rest of his current deal.
There has been no formal offer and no breakdown in talks, with Henderson making it clear that he wants to stay at the club for the rest of his career, but Liverpool's opening proposal has clearly not satisfied the midfielder.
Comparisons have started to be drawn between this situation and that of Georginio Wijnaldum, who let his contract expire this summer after Liverpool refused to offer him a long-term deal on a high wage because of his age.
That was the stance taken for 30-year-old Wijnaldum and there are concerns that Liverpool could feel the same way about Henderson, who is one year the Dutchman's senior and will be 33 when his current deal expires.
Clubs from across Europe have seen their interest piqued by the situation. Paris Saint-Germain and Atletico Madrid are both monitoring the situation, aware that Liverpool's track record suggests a lucrative deal for Henderson may not be forthcoming.
It's worth noting that nobody involved actually wants Henderson to go. He wants to stay, manager Jurgen Klopp loves him and the club's owners also value him highly, but the midfielder has concerns over why those in charge at Anfield actually want to keep him around.
Henderson wants to be at a club where he will play consistent minutes and not simply take up a cheerleader role in the dressing room, and Liverpool's preference to pursue younger players has him concerned that he might not actually be part of the long-term furniture at Liverpool.
He's not yet heading for the exit door, but there is a feeling that Liverpool will not let this drag on and allow Henderson to enter the final 12 months of his deal. If an agreement cannot be reached, the club will start to consider a possible departure.