Adam Webster has already gone – and Ashley Harris is expected to follow.
And Guy Whittingham will look for more of his young Pompey hopefuls to tread the same route by going out on loan in the coming weeks and months.
The Blues boss is expecting a repeat of last season when the club’s development squad were sent out to non-league sides to gain experience.
Jed Wallace and Dan Butler benefitted from time at Whitehawk and Hawks respectively, before returning to the first-team at the start of this year.
Now the same path is set to be taken by the current group of Jack Maloney, Nick Awford, Liam Triggs, Josh Warren and George Branford.
Webster is benefiting from first-team football at Aldershot Town in the Skrill Premier.
And there is some talk Ashley Harris would be receptive to gaining some action at the Recreation Ground.
Whittingham believes it is important to choose carefully when selecting homes for players to continue their development.
He said: ‘We’ve had a couple of enquiries for Ashley.
‘But we have to make sure it’s the right club for him and they are the right club for us.
‘We don’t want to let our players out to somewhere where they are not treated properly. We have to make sure it’s the right move.
‘Ash is not one of those players who can play in a team who just lumps it forward all the time.
‘We have to make sure he’s involved in games.
‘Wherever the right opportunity comes, we’ll look at it for him.
‘There’s more chance of the first-year pros doing what the Dan Butlers and Jed Wallaces did last year.
‘It may be they train with us and go to a lower league side to get some football.’
Webster made his third appearance for the Shots last weekend as they went down to a 1-0 defeat to league leaders Cambridge.
Whittingham kept tabs on the 18-year-old last week, watching him impress at centre-back in the 3-0 win over Dartford.
‘I went to see Adam last week against Dartford and I thought he had a decent game,’ said Whittingham.
‘I think that is great for him, really good.
‘They wanted him as a centre-half and that is where Adam wants to play.
‘He did well and they must be delighted with him.
‘The deal’s until January, initially.
‘They won and he got a clean sheet.
‘He competed well and he’s in the right place to learn his trade while helping Aldershot.
‘It’s vital to watch him – he’s our player.
‘We have to make sure he can fit in with us if he needs to come back.’