Boss Brendan Rodgers is already facing an uphill task convincing star man Raheem Sterling to sign a new deal.
But Starsport can reveal there are also doubts over the Anfield future of influential midfielder Henderson as well.
Henderson has turned down a new contract understood to be worth £80,000-a-week.
More talks are planned but Chelsea are monitoring the situation closely.
Most of the focus has been on Sterling’s very public stand-off with the club after turning down a £100,000-a-week deal and putting all talks on hold until the end of the season.
But Sterling still has two years left on his deal while vice captain Henderson’s case is seen as more urgent as he only has one year left come the end of the campaign.
England man Henderson is now one of Liverpool’s key men, having initially struggled to live up to his £20m price tag after joining from Sunderland in 2011.
Liverpool’s hopes of qualifying for the Champions League with a top four finish are all but over, following Saturday’s 4-1 at Arsenal.
And Rodgers admits that will make it even harder to attract big name signings in the summer.
“I think most players want to be in the Champions League,” he said.
“Players want to play at the top level of the game and if you’re not in the Champions League it makes it difficult for you.”
Asked if Champions League qualification is now gone, following the Gunners defeat and a home loss to Manchester United, Rodgers said: “I think so. I’m a realist as well.
“I think with the two games that we’ve had, I think we needed to take something from Arsenal, and if we’d done that then our chances would have been greater.
“I wouldn’t expect the others to slip up, particularly Arsenal or Manchester United. I don’t expect them to do that.
“Add to that, the sort of growing number we’ve got unavailable I think it will make it very, very difficult with only seven games to go.”
Liverpool’s season now rests on winning the FA Cup, with a quarter-final replay at Championship Blackburn on Wednesday night.
One player who looks certain to leave Anfield at the end of the season is striker Mario Balotelli.
The Italian misfit ruled himself out of the squad for Arsenal.
Rodgers said: “He trained with the team. He had a slight knock and felt he had to come out of the training.
“He felt it was too sore to travel. The medical team looked at it but it was the decision of Mario.”