Here’s a look at four talking points as Danny Cowley steps up the Blues’ latest quest to reach the Championship.
New faces on show
Every manager hopes to have the majority of his squad sewn up for the opening day of the summer.
That's not the case for Cowley as he continues a major Fratton Park rebuild.
Still, the dressing room's looking a lot stronger than this time a week ago when teenager Liam Vincent was the sole signing.
Clark Robertson (Rotherham), Shaun Williams (Millwall) and Ryan Tunnicliffe (Luton) have all been recruited in the past seven days – much to supporters’ delight.
All three are expected to be key members as Pompey look to remove their League One shackles, having played in the Championship last term.
With that in mind, Cowley will likely want the trio on the south coast from day one as he gears up for a crucial few weeks ahead.
Given there are only 16 players under contract, Pompey are presently short of bodies.
Cowley may call upon academy youngsters such as Harry Jewitt-White and Alfie Bridgman to plug a few gaps.
Under Kenny Jackett, it was extremely difficult for free agents to earn deals. Only goalkeeper Duncan Turnbull was successful among a swathe of those who auditioned.
However, Paul Cook opted to take on Ben Davies, Gareth Evans and Brian Murphy.
Pompey's backroom staff is now almost complete after Simon Bassey's arrival as assistant first-team coach was confirmed last week.
However, the Blues are still missing a goalkeeping coach following John Keeley's departure at the end of last season.
As reported, Pompey have been closing in on an appointment and it should be made in time for the first day of training.
That means the new man can work with Alex Bass, who's currently the only senior stopper under contract.
He'll also work with Gavin Bazunu the Manchester City youngster closes in on his move to the Blues.
Should an appointment not be made, academy keeping coach Michael Poke will likely fill in.
Toughest you can imagine
The players will be hoping that the balls will be making an appearance as soon as possible.
After all, they’ve probably not had a kickaround with their mates since the defeat to Accrington on the final day of last term.
However, Cowley may have other ideas.
In April, the head coach gave an insight into his pre-season plans.
Cowley said: We're going to have the toughest pre-season you can ever imagine!
‘I like cranking the treadmill up so high and so fast, it makes the players run harder.
‘By the time they get to the start of the season, the games feel easy because of the challenges they had.'
Judging by what Cowley said, the formative stages of the summer are likely to primarily be focused on fitness and getting his troops into peak shape.