The seven-time European champions are actively reshaping their attacking options after an inconsistent season in front of goal.
As part of that process, the club’s hierarchy have intensified their search for a forward capable of leading the line in the long term.
Jackson, currently contracted to Chelsea, has now moved firmly onto Milan’s radar as they explore potential deals.
The 24-year-old has spent time away from Stamford Bridge, but his situation remains unresolved heading into the summer.
A permanent move elsewhere has yet to materialise, particularly with Bayern Munich not fully convinced about securing his services on a long-term basis.
That uncertainty has opened the door for Milan to position themselves as a serious contender for his signature.
Club officials believe Jackson’s profile fits what they are looking for in a modern striker — pace, movement and the ability to stretch defences.
His previous experience at Villarreal also demonstrated his capacity to develop within a structured attacking system.
Milan’s interest is not just tentative, with reports suggesting they are now closely monitoring his situation as they prepare for a possible approach.
The Italian giants are understood to be evaluating multiple options, but Jackson is increasingly viewed as one of the most realistic and attainable targets.
A move to San Siro could offer the forward a fresh start and a central role in a team rebuilding its attacking identity.
For Milan, securing the right striker is seen as a decisive step in returning to consistent domestic and European competitiveness.
Jackson’s future remains open, but with Milan accelerating their interest, the summer window could present a defining moment for both player and club.