Kenny Jackett is looking to bring in two more players before the close of the transfer window.
But his biggest job this month may just be managing to keep hold of one of the young men he already has in situ.
Jackett has stressed he is under absolutely no pressure to cash in on any his prized assets.
Furthermore, he was insistent on Monday there have been no enquiries made for any of the players currently at his disposal.
Whether that’s still the case in three weeks’ time when it comes to Matt Clarke is a matter of some doubt.
It’s Brett Pitman’s goals this term which have understandably grabbed the headlines in Pompey’s mildly-surprising move into the play-offs.
But there has been no more consistent player for the Blues than the 21-year-old from Suffolk.
The South Stand was closed to the public on Tuesday night for the Checkatrade Trophy meeting with Chelsea’s under-21s.
Yet the directors’ box and surrounding seats were awash with many of the game’s movers and shakers.
The club car park behind the North Stand was also stacked with sports cars and 4x4s as a swathe of agents, scouts, technical directors and decision makers weighed up what was on offer.
Among them was Bournemouth boss Eddie Howe as he did his due diligence ahead of possible January transfer recruitment.
Undoubtedly, it was the galaxy of immensely-rewarded prospects from Chelsea who attracted the majority of those present.
But many of those trained eyes, if they weren’t there for him to some degree anyway, would have left with Clarke’s name circled on their dog-eared team-sheets.
Clarke served up more of what he’s been doing all season against opposition lauded as some of the best, young talents on the planet.
Quite frankly, he made containing them look simple.
When players make the game look as easy and uncomplicated as the defender currently does, you know they are on to something.
The biggest irony – and compliment to Clarke – is someone without knowledge of the players’ dates of birth would never have thought the 21-year-old was facing people his own age.
It was like watching a seasoned pro toying with impetuous upstarts and putting them firmly in their place.
One second-half charge up the pitch – the kind Pompey fans have become familiar with – saw conspiratorial heads lowered and murmuring to each other among the scouts grouped together.
Two-and-a-half years ago, the former Ipswich man took the brave decision to step down from the Championship and head for a fourth-tier netherworld.
So, how apt Tuesday’s game saw Clarke chalk up his 100th senior appearance. In contrast, Chelsea under-21s totalled 13 senior outings across their 18-man squad.
That experience for the Pompey man has been invaluable and it now looks inevitable, one way or the other, Clarke will be moving up the leagues in the not-too-distant future.
Meanwhile, one of football’s biggest concerns remains the game’s big guns stockpiling young talent sold a dream of playing at the highest level they’ll never achieve.
With Clarke’s current contract having 18 months to run, Pompey’s asset remains secure. But, by the same token, hardly nailed down for the long term either.
His partnership with Christian Burgess has been the fulcrum of the team’s solidity under Jackett and will be crucial over the second half of the campaign.
The hope is the club can fend off the vultures waiting to swoop for a talent central to their play-off ambitions – for now.