Rossoneri head coach Sergio Conceicao faces a daunting task in propelling his side closer to the Serie A top four, which was clear to see following a frustrating 1-1 draw with struggling Cagliari last time out.
They arrived in Lombardy to take on a Como team also at risk of relegation, but one targeting a third consecutive home win.
Given the recent confidence Cesc Fabregas’ men would have gained from back-to-back 2-0 wins over Roma and Leece at the Stadio Giuseppe Sinigaglia, it was perhaps unsurprising that there was little to choose between the two teams in an even first half.
Gabriel Strefezza’s speculative strike forced Mike Maigan into a low save at his near post, while Marc-Oliver Kempf headed wide from Lucas Da Cunha’s free-kick in two early opportunities for the hosts.
Milan looked to the talismanic Rafael Leao for inspiration, and he was the architect of two quickfire chances for Tijjani Reijnders and Alvaro Morata, with the duo both denied by home Como debutant Jean Butez.
Conceicao opted for a triple change at the break, introducing Alex Jimenez, Yunus Musah and Tammy Abraham to add a fresh injection into Milan’s attack. And while Jimenez looked dangerous after being introduced, it was the hosts who struck first.
The impressive Assane Diao marked his home debut with his first Como goal, brilliantly cutting in off the right flank and rifling a superb left-footed strike past Maignan at his near post.
At 19 years and 129 days old, he became the club's youngest foreign player to score in Serie A. Maxence Caqueret - making his first appearance in a Biancoblu shirt - came off the bench to provide the assist for Diao with his pass out from midfield.
However, Como’s joy lasted little more than 10 minutes as Theo Hernandez equalised following a defensive scramble with a left-footed volley after Como failed to clear a Milan corner.
It was a historic moment for the France international, who became the club’s highest-scoring defender in Serie A history with 30 goals, eclipsing Paolo Maldini’s total of 29.
The turnaround was complete when Leao added Milan’s second with a delightful dinked finish over Butez after he latched onto Abraham’s perfectly weighted through ball.
Patrick Cutrone went agonisingly close to restoring parity for the hosts, but Maignan was on hand to make a fine save at his near post.
Ultimately, Milan did enough to claim three crucial points which move them to within five of Lazio in fourth. Meanwhile, this defeat for Como sees them drop down to 16th, where they are a mere point clear of the bottom three.
Flashscore Man of the Match: Rafael Leao (AC Milan)