Some tough decisions will be required if the Fratton Park outfit are to return next season with a squad more equipped to challenge for promotion.
And it’s a process that will kick off more or less immediately after Pompey’s final game of the season against Wycombe on Sunday, May 7.
Calls on those first-team players who are now in the final weeks of their contracts have to be made.
But that’s not the start and finish line as far as outgoings are concerned.
The Blues are realistic to know that others within their current ranks could attract interest from elsewhere.
Meanwhile, the decision could be taken to sell others on – those deemed not natural fits for the project at hand.
But what potential departures could we see amid another Pompey overhaul?
We take a look to see what players could realistically be elsewhere by the time the 2023-24 season begins.
5. Kieron Freeman
The defender's Pompey future has been in doubt more or less since October 2022 - just four months after his arrival. He's featured just eight times in the league since a 4-0 defeat to Ipswich on October 29, 2022, with his last League One start coming on February 5, 2022, during a 3-2 loss to Oxford. The 31-year-old is yet to feature under John Mousinho, which begs the question: what's taken so long so say goodbye to the unfortunate wing-back? Photo: Paul Thompson
6. Connor Ogilvie
Like Oluwayemi, there's no guarantee Ogilive will be here next season simply because of his presence on the current out-of-contract list. The chances are he'll be offered a new deal to remain at Fratton Park. But there's always the possibility of another club recognising his consistency levels at League One and stealing a march on the Blues as they take their time over renewals. Photo: Jason Brown
7. Ryan Tunnicliffe
There's no doubt about it, Tunnicliffe deserves huge praise for the way he's turned his Pompey career around. He was well out of the first-team picture at the start of the season but took his chance as midfield injuries and unavailability took their tool around October. The 30-year-old is currently on 37 appearances for the season to date. However, his omission from the team and match-day squad against Accrington last weekend was telling. He's out of contract at the end of the season and the signs are Tunnicliffe will be saying goodbye to Fratton Park in the weeks ahead. Photo: Jason Brown
8. Ronan Curtis
The ACL injury Curtis picked up against Bolton in February has really thrown a spanner in the works. The winger is out of contract at the end of the season - and everything pointed to a Fratton farewell after five years on the south coast. Yet his knee injury could potentially see him sidelined until December. Pompey have come out and said they'll support Curtis with his rehab - but what exactly does that mean? Another new deal? A short-term deal on reduced terms? The use of their medical facilities? No-one really knows - and with that doubt comes additional doubt that any agreement will be reached. Photo: Jason Brown