He’s always said it will take three windows for him to get his side to where he wants them to be.
Well, we’re at that stage now, so the pressure is well and truly on him and the powers that be a Fratton Park to get it right.
Can you imagine the frustrations levels if Pompey are consigned to a seventh successive season in League One?
It doesn’t bear thinking about!
The Blues have kick-started the process by activating the clauses in both Marcus Harness and Louis Thompson’s contracts.
Jay Mingi and Jayden Reid are expected to follow suit, but doubts remain over the futures of Sean Raggett, Aiden O’Brien and Michael Jacobs.
There’s also been plenty of players linked, too, giving Blues fans a flavour of who could be arriving at Fratton Park in the near future.
But when does the window officially open and end?
Here’s the answer to those key questions and others as Pompey supporters wait patiently for the drama to officially begin.
When does the 2022 summer transfer window open?
The transfer market opens officially on Friday, June 10, for all clubs and falls into line with international transfer regulations.
Out-of-contract players can move as free agents before the window opens.
The window opens 10 days before the Blues report back for pre-season training and 13 days prior to the release of the 2022-23 fixture list.
When is transfer deadline day?
The window will close on Thursday, September 1, at 11pm, giving all clubs 83 days period to get their business done.
What deals can be done outside of the window?
Out of contract players can move as free agents before the window opens in June.
Clubs can also announce deals to sign players before the window officially opens – but they cannot be fully ratified until the window opens.
Who have Pompey been linked with?
Even at this early stage, it might be more appropriate to ask who have Pompey not been linked with?
Only two weeks have passed since the final day of the 2021-22 season, yet the rumour mill is churning out names left, right and centre.
Of course, some have to be taken with a pinch of salt.
Meanwhile, others could be true – but could involve players down the priority list.
Among the names The News understands to be legitimate targets are Matt Butcher, Aaron Collins, Will Boyle, Kion Etete and Kyle Wootton.
A return for George Hirst is also a priority, as are attacking players with pace, power and athleticism.
Others linked with a summer move to Fratton Park include Cole Stockton, Kyle Joseph, Lynden Gooch, Luke Molyneux and Morgan Whittaker.
What’s Pompey’s finances like this summer?
Well, we all know Danny Cowley was hamstrung last summer after inheriting a squad with some big earners.
The players released at the end of the 2020-21 season helped generate some room for manoeuvre, but those who remained still limited his spending power.
Further finances were generated by letting the likes of John Marquis, Lee Brown and Ellis Harrison leave in January.
Meanwhile, the pot will likely be added to when the final decisions are made on the 10 remaining out of contract players.
Chief executive Andy Cullen has already stated the Blues’ budget this term will remain ‘competitive’.
He also added that the Blues are ready to up their transfer spending to get the key additions Danny Cowley needs this summer.
Whether it proves enough to deliver promotion, however, remains to be seen.
How many new faces can we expect?
Danny Cowley wants to keep up to 17 members of the squad that finished the 2021-22 campaign.
And with the Pompey boss working to a squad size of 22, plus youngsters, that allows for at least five summer signings.
That could be more, though, given the uncertainty around Marcus Harness’ future – despite the club activating a one-year extension on his Fratton Park deal.
Meanwhile, it remains to be seen if that figure of 17 can be reached.
Of the 12 players deemed out of contract on the final day of the season, only Harness and Thompson deals have been struck, taking Pompey’s existing senior numbers up to 12.
Jayden Reid and Jay Mingi are expected to follow, yet doubts remain over Sean Raggett, Aiden O’Brien, Michael Jacobs and Reeco Hackett, to name just four.
Shaun Williams is expected to leave after one season at Fratton Park.