Adam May is currently on trial at Crawley Town.
The midfielder’s hoping to impress Reds boss John Yems and earn a loan switch to the League Two side for the rest of the campaign.
May, who is out of contract at the end of the season, returned to Pompey earlier this month following a frustrating spell at Swindon.
Despite joining the Robins on a season-long loan in the summer, he was confined to a bit-part role.
May made 13 appearances for the fourth-tier leaders, with only five coming from the outset.
The Blues are keen to send the academy graduate back out on a temporary basis for the remainder of this term – with Crawley potential suitors.
Pompey assistant manager Joe Gallen said: ‘Adam is currently on trial with Crawley. He is there with a view (to join them on loan).
‘He needs to get back playing football. Adam went to Swindon hoping to play but didn’t, so he needs to get out and play some games to get his career going.
‘If Adam is happy to go there then I hope it comes off for him because he needs to start playing.
‘He has got a lot of ability but players need a certain amount of games, which he needs.’
May has made 29 appearances for Pompey since his debut in April 2015.
The majority of his outings arrived after Kenny Jackett took the helm from Paul Cook.
He was on Wolves Academy’s radar when Jackett and Gallen were in charge at Molineux.
And despite May – who is out of contract at the end of the campaign – being down the pecking order at Fratton Park, he’s still held in high regard.
Gallen added: ‘Adam was one of the players we knew about when we arrived.
‘Players have come in and got ahead of him. He did play some games and played well at times.
‘Again, maybe we’ve just had better (options). Everyone likes Adam May and we all want the best for him – hopefully this one comes off.’