Liverpool fell to defeat in the first match of their pre-season tour of Asia after old foes AC Milan exploited poor defending to beat the Premier League champions 4-2.
The Reds fell behind early to a Rafael Leao strike before Dominik Szoboszlai equalised.
Noah Okafor scored two after the break and Ruben Loftus-Cheek was also on target for the Italians, while Cody Gakpo scored a consolation goal for Liverpool.
Arne Slot's men now jet on to Tokyo for the second leg of their tour and the boss has plenty to ponder – with both positives and worrying signs to come out of this game.