Marlon Pack has been told he has no Pompey future.
Steve Cotterill delivered the news to the young Buckland midfielder this week after deciding against giving him a new contract.
Pack is now expected to thrash out a permanent deal with Cheltenham after impressing during his season-long loan at Whaddon Road.
It signals the end of a Fratton Park stay for the midfielder, who has been at his local club since the age of eight.
He joins teenager Tom Kilbey in not being awarded a contract extension when his existing deal runs out this summer.
The futures of other youngsters such as Billy Goddard, Perry Ryan, Peter Gregory and Ellis Martin are yet to be decided.
Pack made two Pompey appearances this season before being loaned out to League Two Cheltenham.
Cotterill believes the 19-year-old will not get the regular football his development needs by staying at the Blues beyond this campaign.
He said: ‘Cheltenham have offered Marlon a contract for next season and he came to see me the other day and wanted to know where he stood.
‘I have told him he won’t be getting a longer contract here.
‘I have been down and seen him enough at Cheltenham this season and he needs to play.
‘He’s going to play more regular football in League Two than he will in the Championship at this moment in time for Portsmouth.
‘I don’t really want to go public on the ins and outs but he is another very nice, sensible boy who understood what I said to him and even gave answers to some questions he could have asked me.
‘What has happened is he has been here since he was eight and it’s a wrench for these younger players.
‘I said to him we could go the other way and he could sign another contract for another year here, not play in the team and potentially not go out on loan.
‘But where is that is going to take him? What is that going to do for him?
‘Like Tom (Kilbey) and Matt (Ritchie), they have all been let go with the right purpose in mind for their future.’
Pack has featured 34 times for Cheltenham this season, scoring twice.
He has been a regular in the centre of midfield, catching the eye with some impressive displays.
That has led to the Robins seeking to make the teenager’s stay a permanent one.
Pack has also enjoyed several other successful loan spells during his time at Fratton Park after he spent time at both Wycombe Wanderers and Dagenham & Redbridge last season.
The midfielder returned to feature in Pompey’s pre-season tour to America and Canada, scoring against Ventura County Fusion.
He went on to make his first-team debut as a substitute in the Carling Cup victory over Crystal Palace at Fratton.
The following match he featured as a substitute against Cardiff City in what was his final Blues appearance.
Now his footballing future looks to be with Cheltenham.
Cotterill added: ‘Marlon has had a similar season to what Portsmouth Football Club have.
‘Basically, that is not a very good start, has done well in the middle, had a little bit of a dip, and has come on again.
‘I have seen him play a few times at Cheltenham in a few different positions.
‘Sometimes with a diamond in midfield, sometimes playing with a three, sometimes playing with a two.
‘What we have got to bear in mind is it’s a different league.
‘So Marlon, being a decent footballer, should continue to do well and shine in that league.’