Christian Oxlade-Chamberlain has switched to Oxford City as Pompey drive ahead with his right-back development.
Blues boss Kenny Jackett has earmarked the central midfielder for conversion into an attacking full-back.
Following a month at Poole Town, he has now made a loan move to fellow National League South outfit Oxford City.
The six-month temporary spell is on the understanding Oxlade-Chamberlain is given opportunities at right-back.
And Pompey will be monitoring the 19-year-old’s Marsh Lane progress.
Oxlade-Chamberlain, brother of Liverpool and England’s Alex, made six appearances for Poole during the opening month of the campaign.
That included a scoring debut, coming off the bench to net in a 2-1 win over Weston-super-Mare on the opening day of the National League South season.
However, he started only three times for Tom Killick’s side during a loan for an initial month.
Now he has swapped sides in the same division, linking up with 19th-placed Oxford City.
Boss Mark Jones told the Oxford City website: ‘I have seen him play this season and was very pleased with what I saw.
‘He is a player with big potential and we’re excited to help him develop.
‘Hopefully he can come and help us with the problem area at right-back, so it is a mutual benefit for both sides.’
Oxlade-Chamberlain is contracted at Fratton Park until the summer of 2018 after Pompey took up a 12-month option in July.
However, he appeared just once in pre-season under new boss Jackett, climbing off the bench in the 59th minute during an 8-0 win at Newport Isle of Wight.