Last pre-season, high-profile players such as Tom Naylor, Jack Whatmough, Craig MacGillivray, and Ben Close failed to extend their stays at Fratton Park.
With Danny Cowley at the helm for exactly a year, he’ll now have to decide who stays, or who goes for free at the end of the season.
Here’s the latest on each’s future – and who Blues writer Sam Cox believes should be handed new contracts.
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5. Michael Jacobs -Yes
With the option to extend his stay by a year, Pompey should keep Jacobs at the club until the end next year. If he stays fit he's one of the most creative players at Cowley disposal, and they can't afford to pass quality to League One rivals again this summer. Photo: JPIMedia
6. Reeco Hackett - Yes
Hackett has found himself in a difficult position in terms of contract extensions. His clause looks unlikely to be triggered due to the wage increase it would provide, although the club wish to keep him. Regardless, he's showed he can cut it in League One and should be offered a new deal. Photo: The News
7. Paul Downing: - No
Pompey's position on Downing was made clear in January as they allowed him to leave on loan to Rochdale. Shouldn't and won't be offered fresh terms. Photo: JPIMedia
8. Callum Johnson (On loan at Fleetwood Town) - No
Similar to Downing, the club's position on Johnson was made clear last summer. Should be allowed to seek a free transfer in preseason. Photo: JPIMedia