Jackson has reunited with former Dikwena coach Owen da Gama at Highlands, having been released by Stars along with Cavin Johnson in July 2017 prior to the club's ill-fated Absa Premiership campaign last term, which ended in relegation.
The 46-year-old played under Da Gama when Silver Stars won the Telkom Knockout in 2006 when a key figure at the club was Larry Brookstone, who is now a director at the Lions of the North.
"I'm delighted to be part of the Highlands Park team, but this is not new to me because I have worked with a lot of players previously at Platinum Stars in the MDC team before," Jackson tells snl24.com/kickoff.
"The only challenge is that the team has just come from the NFD to the PSL, but they've got a lot of youngsters that are playing in different age groups in the development leagues.
"But remember two seasons ago they were also in the PSL. They had a MDC team and most of the young players were playing in the Castle League, some of them were in the MDC team that time.
"But ja, I'm going to work with a lot of youngsters and it is just to promote the guys for the coach [Da Gama] to have a look at for the senior team and for others that come back and play in the MDC."
Meanwhile, Jackson, who spent 14 years with Dikwena, was sad to see the Phokeng-based club suffer relegation.
"Obviously we are all saddened at them being relegated to the NFD after working so hard in the team as a player and also as a coach," says the one-time Orlando Pirates defender.
"We were the first club in South Africa [in 2008 at Lucas Moripe Stadium] to beat Al-Ahly [2-1 in the preliminary round of the CAF Champions League in the first leg before losing 2-0 away]. I was still a player at that time.
"The club has got some history with me, we won cups. I won the Telkom Cup as a player and as well as an assistant coach. We did a lot but unfortunately I don't know what happened last season.
"The manager [Senzo Mazingisa] told us [Jackson and Johnson] that he'll not renew our contract and he let us go, and they want to bring new people in. It is unfortunate now that they're going to be playing in the NFD.
"I don't know if they'll still be based in Rustenburg or move elsewhere next season. I just feel sorry for some of the players and some of the guys at the club. We're all very saddened by it."