Despite being grateful for a solid grounding in the game at Middlesbrough, a senior debut proved frustratingly elusive for the 23-year-old, who had to watch from the periphery while fellow left-sided defender Ben Gibson made it big with the Boro.
Refreshingly, Jackson is not one to harbour any grudges at failing to make the first-team grade during his five-year stint on Teesside, but it will be a sweet moment nevertheless if he can make his first-team return at a place he knows well today.
His previous Riverside experience came in front of the equivalent of one man and his dog, playing in front of a few sparse crowds for the reserve and youth side on the odd occasion and also in a couple of pre-season friendlies – where the competitive edge was somewhat diminished.
The Darlington-born centre-back, who joined the Reds in August, 2016, said: “I played in a couple of friendlies and a few youth team games and Under-18s and reserves. But never a first-team game.
“I was on the bench a few times, but not at the Riverside – it was a few away games in the Championship and cup games.
“It would be really nice to play in front of a big crowd. I have played there and it has been empty.
“It will be nice to play in front of a good atmosphere. I am sure that there will be a few Barnsley fans going as well to make it nice and loud. It will be brilliant.
“A few of my family and friends will be there and I am not sure which way they will be wanting it to go this week!”
Despite being starved of first-team opportunities, Jackson believes his back-four education was significantly enhanced by his time at Boro, where he worked under the tutelage of a couple of accomplished centre-backs in Tony Mowbray and Aitor Karanka.
The latter was particularly well known for his fastidious attention to defensive details, with Boro breaking several records during their promotion season of 2015-16, with Jackson being grateful for the input of both Karanka and his predecessor.
Even if he could not progress in the manner of his former colleague Gibson.
Jackson said: “There was Karanka and Tony Mowbray was there as well and he used to be a defender and both of those two played a lot of first-team games and it gave me a grounding and understanding of what they expected. Obviously, I never played, but you could tell in training what you needed to do.
“Ben was quite lucky and got out quite early on loan. He did not have a great loan spell at Plymouth when they were at the bottom of League Two and he even admitted it was a bad move for him as he did not play well. But he admitted it was the best loan as he learned straightaway at 17 or 18.
“He came back, went on loan again and kicked on again. Ben was always one of the best players in the youth team and always a stand-out and everyone knew he was going to make it. He definitely deserves it.”
After missing the midweek game at Cardiff after a mandatory seven-day break from first-team training and matches on medical grounds following his concussion in the previous game with Hull City, Jackson is particularly keen to make up for lost time, more especially after only recently returning from a knee problem.
The north-easterner, stretchered off with a head injury following an 11-minute delay after a sickening clash of heads with Hull counterpart Jon Toral amid worrying scenes, said: “I am loads better now.
“For the first couple of days, I was a bit groggy and had a headache and did not feel too well. But I got better day by day and, in the last couple of days, I have felt fine and back to normal.
“Especially after getting back in the team and playing the last couple of games, it was really annoying. But rules dictate I could not play and that is fair enough.
“The focus now is to get out of the trouble and everyone has bought into it straightaway. I think part of the reason we are a good group is that we are young and hungry and we want to get better.
“To be honest, if we keep doing what we are doing, I do not think we will be a million miles away.”