It’s a decision that’s caused debate among Pompey fans.
The Blues have decided to shelve any contract talks until the end of the season as they target promotion into the Championship.
The deals of Ronan Curtis, Christian Burgess, Brett Pitman, Lee Brown, Brandon Haunstrup, Oli Hawkins, Luke McGee, Anton Walkes, Adam May and Matt Casey all come to a close on June 30, 2020.
Some are first-team regulars, others are on the fringes of things.
Regardless it’s an approach not without risk – especially as the caveat to such a strategy is still fresh in the memory.
Despite Pompey claiming the League Two crown when the same tactics were used in 2017, some members of the Fratton faithful still believe it’s why Enda Stevens left at the end of that campaign.
And when it comes to Nathan Thompson, another example that’s been aired, it was the player himself who decided to shelve contract talks.
The Blues wanted to keep him last summer, but the right-back decided he'd try to find a Championship club – which failed to bear fruit for the now Peterborough defender.
The prized asset whose contract expires at the end of this season is Curtis.
Arriving from Derry in June 2018, the £100,000 transfer fee has proved a bargain and a gamble that has paid off.
The Republic of Ireland international will hold aspirations of playing in the Championship.
If the Blues do build the head of steam required to yield promotion, there’d be little reason for Curtis to seek a move elsewhere.
Should Pompey be confined to another year in the third tier, the club do hold the club option of an additional 12 months.
Fans’ favourite Burgess is into his fifth campaign at Fratton Park.
As things stand, he’s first-choice centre-back, despite being earmarked for a place on the bench before the season kicked-off.
But regular minutes and an affinity for the south coast means he may be happy to wait.
Part of Brown's reasons for living Bristol Rovers for Pompey was to be closer to his native London.
The vice-skipper has already stated he’s relaxed about his situation and wants to extend his stay at the club, so he’s another who won’t cause too much concern.
Hawkins is a versatile figure, capable of operating in both striking and defensive roles – and that shouldn’t go underestimated when it comes to squad planning.
What could be key behind Hawkins remaining at PO4 is if Jackett remains as manager.
Yet with all the recent noises leading to that conclusion, fresh terms for the 6ft 5in player will be tabled.
As things stand, those are the players who you’d predict will be here for the 2020-2021 season – but the waters are slightly murkier when it comes to the rest.
Pitman was the marquee signing from Ipswich during Jackett’s first summer in charge in 2017.
While the prolific marksman took a pay cut to drop into League One from Ipswich, his three-year deal still made him the top earner at the time.
It’s unlikely the former AFC Bournemouth forward could barter such terms again as he approaches his 32nd birthday.
And while he finds himself on the bench more often than not, Pitman may want to again play week in, week out as he begins to approach the twilight years of his career.
Haunstrup turned 23 last month, yet only made his 50th appearance at Harrogate and is frustrated over his lack of game-time.
Conor Chaplin is another former Fratton youth product, but departed to fulfil his ambitions of playing regularly and is currently reaping the rewards at Barnsley.
That's a pathway Haunstrup could look to imitate himself – and you could hardly blame him.
It’s inevitable McGee will seek pastures new.
Signed to be No1 keeper from Spurs in 2017, he’s now slipped to third in the pecking order behind Craig MacGillivray and Alex Bass and wanted to leave last the summer.
Then there is Anton Walkes and Adam May, with the club holding the option of an additional year on both.
The latter is struggling to feature on loan at League Two Swindon, while Walkes has been on the periphery of things for most of the season.
With Tom Naylor and McCrorie sidelined with hamstring injuries, Walkes has an opportunity to now stake a midfield claim after struggling at right-back at the beginning of the campaign.
Overall, what could be crucial to who’s retained depends on Pompey’s recruitment during the January transfer window.
Chief executive Mark Catlin revealed Jackett is looking to bolster key areas of his squad to propel the Blues up the table.
It may be unsettling times for those out of contract at the end of the season, as they won’t have the security of their next move.
But the Blues are right to delay negotiations as promotion is prioritised.