Salary cap and squad number restrictions, coupled with the crippling costs of coronavirus, meant talks had been initiated with some of the 11 first-team players whose deals expire at the end of the season.
However, there was never any chance of that dialogue becoming more than just that – discussions – with pay cuts the only option realistically presented to players in that stage of negotiations.
The shackles have, of course, come off after an independent arbitration panel upheld a claim from the Professional Footballers’ Association (PFA) that the EFL was in breach of the constitution of the Professional Football Negotiating and Consultative Committee (PFNCC) by introducing squad salary caps.
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That gives Pompey the freedom to re-enter talks at a level in keeping with player expectations.
That remains a key factor in all negotiations, along with which division Pompey will be operating at come next season. Will manager Kenny Jackett still be around must also be taken into consideration.
It, therefore, means Pompey will continue to tread carefully and not rush into anything.
From left: Jack Whatmough, Tom Naylor and Andy Cannon
But where do their priorities lie? Who who will they be targeting first in their bid to resolve futures? And who might be told that no offer will be on the table regardless of finances?
Here, we take a look at each individual’s own situation and rank them in priority for Pompey.
Tying Naylor down to a new deal has to be Pompey's top priority - irrespective of what division they might be in next season. It's early days, but he's the leading candidate to be the player of the year, making Jackett's decision to drop him for the play-offs even more unbelievable. Naylor's displays won't have gone unnoticed, though, and the Blues might have competition for his services.
Whatmough's past two performances won't have done him any favours - two own goals and a red card. But there's no denying the centre-back has been the Blues' most consistent performer this term. His presence will certainly be needed next season if promotion is not achieved, while he'll no doubt be able to step up to the Championship if that goal is achieved. At 24, he's also only going to get even better. Best agree terms now before others come sniffing.
Few would dispute Pompey appear in safer hands when the Scot is in goal. He rarely lets the Blues down - and there's no reason why that would change next season. Championship football might enhance competition to be Pompey's No1, though, with Pompey likely to reassess their options to avoid this season's issues. That could tempt the 28-year-old to move on but by acting now that could be avoided.
With Pompey having an option on the midfielder, tying him down to next season now makes him less of a priority. However, the 24-year-old is currently enjoying his best run in the Blues team and has established himself as a key performer. He appears to be enjoying his football, which is benefiting Pompey. Offering him new terms would enhance his confidence even more - and probably boost the Blues' promotion hopes.
Goals have been the Aussies' Achilles heel throughout his second spell at P04. Six in 66 appearances is simply not enough. Williams, though, remains a key player to this current Blues team, with his work-rate and versatility a valuable asset. Under Jackett, he would continue to be utilised regardless of the division. A new manager might question his goals and assists tally, however.
With the Blues having an option on the full-back, there's no mad rush to get this one done. Although, there's no doubt the highly-rated youngster will remain on the books at Fratton Park. Others will take priority, but that doesn't mean sorting the 18-year-old's isn't important.
A new deal for Ben Close will be way down the pecking order - although that doesn't mean one will not be offered. The 24-year-old has seen his game time severely limited this season, but his recent goalscoring cameo appearance against Wimbledon shows he still has a lot to offer. He remains a solid option to call upon when needed. The question is: will he be happy with another bit-part role next term, or will he want a move elsewhere to kick-start his career?
It appears Daniels has already established himself as Kenny Jackett's first-choice left-back, with the January arrival starting the past three games. There'll be no mad rush to extend his current short-term deal, though, just because the salary cap has disappeared. There will certainly be a wait-and-see approach to this one, despite Daniels' CV.
The option Pompey have on the American goalkeeper makes this a less pressing matter to sort. Meanwhile, the Blues will need to assess whether they actually see a future for the 22-year-old at Fratton Park. If they do activate their option, expect the University of Notre Dame graduate to head back out on loan to get some much-needed game time.
Jordy Hiwula's lack of game time since arriving on a free in October says it all. Although another short-term deal was agreed in January, it's highly unlikely either party will want to stick to the current arrangement come the summer. He clearly hasn't done enough to convince Kenny Jackett of his capabilities. Who is to blame for that is anyone's guess.
It's fair to say that Morris has played his last game for Pompey. He did well to return to the first-team set-up after a frustrating injury lay-off. But he was unable to build on the manager's expectations after his surprise recall for last season's play-offs. The 24-year-old was well down the pecking order when his loan to Northampton was ratified in January. It's hard to imagine a way back for him at Fratton Park.