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.
9. Ipswich - 6
Out-of-contract players: Massimo Luongo, Joel Coleman, Sone Aluko, Richard Keogh, Kane Vincent-Young, Nick Hayes. Photo: Alex Davidson
10. Forest Green - 6
Out-of-contract players: Ben Stevenson, Dylan McGeouch, Udoka Godwin-Malife, Baily Cargill, Lewis Thomas, Harvey Bunker. Photo: Pete Norton
11. Derby - 7
Out-of-contract players: Jason Knight, David McGoldrick, James Chester, Craig Forsyth, Curtis Davis, Richard Stearman, Scott Loach. Photo: Michael Regan
12. Bolton - 7
Out-of-contract players: Jon Dadi Bodvarsson, Elias Kachunga, MJ Williams, Josh Sheehan, Joel Dixon, Kieran Lee, Lloyd Isgrove. Photo: Tom Dulat