A swathe of names have been linked as Danny Cowley plots the Blues’ latest attempt to remove their League One shackles.
To date, Pompey have staggeringly been credited with an interest in a total of 27 players.
Some such as Owen Dale and Joe Morrell we know Cowley's keen on, some like Clark Robertson and Shaun Williams have already arrived, while others, including Viv Solomon-Otabor, are wide of the mark.
The latest name on the head coach's reported shopping list is Jamie Allen.
Coventry are supposedly willing to allow him a departure, which has apparently alerted the Blues.
And whether a south-coast switch materialises remains to be seen.
However, what the Fratton faithful can take encouragement from is that Allen's position is something Cowley's finally keen to address.
During Kenny Jackett s time at the PO4 helm, a frustration among large sections of supporters was that he never struck upon a quintessential protagonist to fulfil the number-10 role.
In the former manager's favoured 4-2-3-1 formation, a natural conduit between midfield and the striker continually eluded.
It's a valid argument that Jackett's emphasis in favouring his attacking midfielder to have energy and work-rate – rather than panache and swagger – was a key reason why he failed to get Pompey promoted time and time again.
A lengthy list including Kyle Bennett, Connor Ronan, Brett Pitman, Kal Naismith, Conor Chaplin, Gareth Evans, Andy Cannon, Marcus Harness, Michael Jacobs and even Oli Hawkins all auditioned but came up short.
In truth, Jackett only signed one archetypal player to fit the role in Louis Dennis.
That, though, proved a non-league gamble that well and truly failed to pay off. The ex-Bromley forward made just one substitute appearance in the third tier and is now a free agent after being released by League Two Leyton Orient.
Of the bevy of previous candidates, Evans proved the most adept during the first half of the 2018-19 season when Pompey topped the table.
Yet that was because Hawkins provided a focal point leading the line, allowing the fans' favourite to break beyond and make late darting runs into the box.
When playing with John Marquis in 2020-21, though, Evans didn't have the same impact.
Harness spoke about his enthusiasm to feature in the berth at the start of last season, having held discussions with Jackett.
A scintillating hat-trick at Burton as a second striker left the Fratton faithful purring - but he was pushed back out wide weeks later.
Meanwhile, Jacobs was brought in to finally be the solution to the perpetual problem last September, spelling the end of Evans' five years at the club.
However, instead of being the answer, Jacobs' time in a central role proved a brief experiment.
He started only once as a number 10 – a 2-1 defeat to crisis-club Wigan – before his subsequent outings when fit all arrived in his favoured spot on the flank.
For large parts of the 2020-21 campaign, Williams was handed the mantle.
The Aussie never lacked effort or verve but, like the majority of his predecessors, lacked end product. He finished with only five goals in 49 appearances before his exit to Oxford.
As things stand, Pompey have no recognised player to fulfil the berth.
Harness is the most obvious candidate but is preferred out wide, Jacobs is yet to return from injury and been linked with Ipswich, while Ronan Curtis has proven he's at his pinnacle on the left.
Meanwhile, Reeco Hackett-Fairchild's got to firstly display he's up to League One standard, having had a difficult time since arriving 18 months ago.
But how badly do Pompey need a flamboyant, creative attacking midfielder who's at the heart of most forays and weighs in with a decent chunk of goals and assists.
Jack Payne was linked with a potential Cowley reunion earlier this summer, having worked together at Lincoln.
Allen's name cropping up has been greeted favourably by fans, having helped Coventry claim the League One crown in 2020.
However, he reportedly would prefer a move back to the north west if he departs the Sky Blues.
Still, this needs to be the summer the long-standing predicament needs resolving.