Paul Cook is keen to bring the Sheffield United right-back to Fratton Park this summer.
But that process is being slowed by Freeman reaching a compromise over his existing deal.
The defender has been transfer-listed at Bramall Lane following the arrival of Chris Wilder at the club.
Cook is a big fan of the 24-year-old, who made seven appearances on loan with the Blues last term.
Ronan Curtis' Portsmouth future spelt out by trusted source well in the know - with advice on where to play Irishman added, too
Former Portsmouth keeper Alex Bass suffers tough night on and off the pitch as he makes Sunderland debut following Fratton Park exit
Portsmouth boss Danny Cowley makes transfer admission as former Luton and Millwall midfielder edges closer to Fratton Park exit
Portsmouth's Miniesta bidding to live up to big reputation - and those comparisons with ex-Barcelona and Spain star
Former Portsmouth, Ipswich and Bristol Rovers striker joins Port Vale - just eight months after moving to Fleetwood
A move hinges on Freeman coming to an agreement with the Blades over the remaining 12 months of his contract.
His prospects at Sheffield United look bleak under Wilder, though, with one of his first acts as manager to say he wasn’t wanted.
Pompey are staying quiet on talk of a bid for the man who made 22 appearances for his parent club last term.
When asked about interest in Freeman, chief executive Mark Catlin said: ‘He’s still a Sheffield United player and we don’t speak about players from other clubs.’
Meanwhile, the dates of Pompey’s Irish tour fixtures have been confirmed.
Meetings with Cook’s old club, Sligo Rovers, on Wednesday, July 6 (6.15pm) and Bohemians on Saturday, July 9 (3pm) have now been announced.
The Rovers friendly will open Pompey’s pre-season programme and also be a testimonial for their defender Gavin Peers.
Those games are part of a training camp across the Irish Sea that will take place from July 4-10.
That completes the Blues’ pre-season programme, with games also lined up against the Hawks, Sutton, Salisbury, Bournemouth, Bognor and Bristol City.
– JORDAN CROSS