Having missed more games than he's played in the Reds' gradually improving season, England boss Roy Hodgson will soon have to decide whether the reliable 25-year-old centre midfielder is worth picking for the 2016 European Championships.
At the start of 2016, it appeared Henderson had recovered well from heel and foot problems but knee ligament damage suffered against Borussia Dortmund on April 7 cast doubt on not only his starting spot for England but on whether he will make the squad at all.
Jurgen Klopp has stated that his captain will need to play in the last Premier League match of the season to be considered for the Europa League final against Sevilla on May 18.
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The German said about Henderson's own motivation to make the squad: "I saw in his eyes he thinks he has a chance" and that is typical of the ex-Sunderland man's determination to succeed.
Worryingly for him though, England are certainly not short of options in the middle of the park and a half-fit Henderson shouldn't be taken ahead of similar players who are in peak condition and have had played a full Premier League season.
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With only three assists all year, Henderson won't be able to force his way in front of a number of Englishmen who have enjoyed incredibly creative campaigns.
Englishmen with most assists:
James Milner - 11
Dele Alli - 9
Ross Barkley - 8
Daniel Drinkwater - 7
Marc Albrighton, Adam Lallana, Troy Deeney, Jamie Vardy - 6
Jonjo Shelvey - 5
Aside from Albrighton, Deeney and Vardy, these are all players Henderson would be in direct competition with, suggesting England's engine room is pretty well fueled.
So if Henderson wouldn't be able to oust those who are going to be creating opportunities for Harry Kane, Wayne Rooney and Vardy, will he be able to sneak ahead of Tottenham's Eric Dier?
Dier, 22, has missed just one of Spurs' games this year and has provided the rigidity that has allowed Alli and Kane to roam and become England's most important attacking players.
Hodgson would be foolish to cast aside a young partnership that nearly brought Premier League success to White Hart Lane but there will always be the possibility of Hodgson reverting to type and playing it safe.
So few caps
Picking Henderson may sound like the risk-free choice but with just 23 caps, he is still relatively inexperienced on the international stage.
In this incredibly young team however, that number is the sixth highest in England's latest squad and as tempting as it is to throw the youth in the deep end, for practicality's sake there will have to be one or two steady influences in the side.
After an exceptional season Milner will be favourite to fill that role but should he get injured, Henderson would surely be the next authoritative midfielder to select.
The discussion of Henderson's capability in the middle of the pitch may actually prove to be redundant if Hodgson tries to expand his wide options.
Even though the England gaffer will inevitably play Lallana, Vardy, Danny Welbeck or Danny Sturridge as makeshift wide men, he might benefit from including some players whose actual position is the right or left flank.
Marc Albrighton has been resurgent at title-winners Leicester City this year and with more crosses than anyone else in the Premier League he could be an unexpected inclusion as one of England's few genuine wingers.
Andros Townsend is another who could add more balance to a squad that is congested in the middle but realistically his or Albrighton's selection would be just as much a risk as picking Henderson with a dodgy knee.
It'll be tough to leave out a player like Henderson as he has had a difficult time proving to critics that he is capable of playing at the very highest level but if he can't prove his fitness in the short time available to him, he really can't go to a major tournament.
Henderson's selection is far more likely than another injury-plagued midfielder, Jack Wilshere, but he still faces an uphill battle to show he will be a more feasible pick than any of his teammates.
Hodgson has suggested he may only take seven defenders, leaving more flexibility to choose different midfield players and, at the moment, that might well be Henderson's saving grace.
With such an uncertain starting lineup, competition for places is as high as it has ever been and whoever Roy gives a ticket to, the England squad will be more unpredictable and exciting than ever.