Matt Casey has been challenged to ensure he becomes a regular starter when he finds a loan club.
The centre-back is set to temporarily depart Pompey in the next coming weeks after recovering from a dead leg he sustained in the pre-season win at Woking.
The Blues ideally want to get Casey to a National League side to help his promising progress.
The Botley talent spent a large portion at Gosport Borough last season and helped them avoid relegation from the Southern League division one south.
However, Casey had a fruitless spell at Weymouth at the beginning of the campaign, as he struggled to break into the starting line-up.
Jackett admits the first-year professional could find himself in a similar position this term – but it’ll be Casey’s job to be in the XI week in, week out.
The Pompey boss said: ‘Matt Casey has been out with a dead leg but he will go out on loan.
‘Weymouth wanted experience again but he has progressed again and got stronger.
‘It’s never easy to get into any team. When you say go out on loan, no-one can guarantee they play.
‘They've just got to go and you’ve got to hope it works out as a manager.
‘In the end, though, the player has got to be good enough and find a way to get into the team.
‘That is part of it. There are no guarantees but the ideal is he goes out, earns that spot, keeps it and progresses in men’s football.’