And D-Day is approaching for John Mousinho to make his final decision on the futures of the likes of Clark Robertson, Connor Ogilvie and Louis Thompson.
The Blues are expected to have another squad rebuild after another failed season has seen them miss out on promotion from League One.
But what are the contract situations of players from clubs elsewhere in the division?
Using Transfermarkt, we’ve taken a look at the sides with the most men without a deal beyond this season in the third tier to see where Pompey rank.
Here’s what we found.
17. Cheltenham - 8
Out-of-contract players: Ryan Broom, Liam Sercombe, Ryan Jackson, Charlie Raglan, Charlie Brown, Christian Norton, Dylan Bakers, Shaun McDonald. Photo: Pete Norton
18. Charlton - 9
Out-of-contract players: Michael Hector, Macaulay Bonne, George Dobson, Sean Clare, Ryan Inniss, Albie Morgan, Terell Thomas, Nathan Harness, Aaron Henry. Photo: Naomi Baker
19. Port Vale - 10
Out-of-contract players: James Wilson, Ben Garrity, David Worrall, Jamie Proctor, Mal Benning, Dan Jones, Tom Pett, Dennis Politic, Aidan Stone, Sam Robinson. Photo: Gareth Copley
20. Exeter - 10
Out-of-contract players: Archie Collins, Josh Key, Jevani Brown, Jamal Blackman, Jack Sparkes, Gary Woods, Kevin McDonald, Harry Lee, Jonathan Grounds, Pedro Borges. Photo: Pete Norton