The Blues boss is challenged with trimming unwanted members of his first-team squad before receiving the green light from owners Tornante to recruit.
As ever, the situation is not straightforward, particularly considering Pompey are keen to offload a number of high earners ahead of their contracts expiring this summer.
The vast majority of League One and League Two clubs are unable to get close to matching the current wage levels enjoyed by the likes of John Marquis, Paul Downing and Ellis Harrison.
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Yet he admits it’s an ongoing complicated process as the transfer window approaches the end of its first week.
Pompey’s boss told The News: ‘Somebody has got to want the players, then the players have got to want to go.
‘There are always three parties involved – and we all want our own way!
‘Think of buying a house, times it by ten, and that’s how complicated it gets, unfortunately. It shouldn’t be that complicated, but somehow it is.
‘It can move so quickly and there is interest in a number of our players.
‘However, they are human beings and, rightly so, you have to treat them with the respect they deserve - and clubs must want to take the players, haven’t they.
‘We’ve had this before at other clubs and, from our point of view, you would like to do your business quickly.
‘That goes without saying because we know that the players we want won’t be available forever.
‘You get everything in place and when something does happen and frees some money up, then we can press the button.’
Harrison, Downing and Marquis all arrived in the summer of 2019 as Pompey sought to reinvest money from the sales of Matt Clarke and Jamal Lowe.
Marquis (£1m) and Harrison (£425,000) were purchased, while Downing arrived on a free transfer from Blackburn.
The trio have endured frustrating times at Fratton Park, with Harrison and Downing, in particular, hampered by lengthy injury spells.
All remain part of Cowley’s first-team squad and were named on the bench for Monday’s goalless draw at Cambridge United.
Cowley added: ‘It is challenging, of course.
‘Covid has changed the goalposts, as we know, and we are ready to act as soon as we get the opportunity.’
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