Technical director Paolo Maldini and sporting director Frederic Massara have signed two-year contracts at Milan, the club confirmed on Friday.
The pair’s previous deals had expired on Thursday with the end of the 2021-22 season.
However, Maldini had belatedly confirmed he would be staying at the club following a tough start to the close season.
Although Milan won the Serie A title last term with a team built in part by Maldini and Massara, they have struggled to add reinforcements for the coming campaign.
With the Rossoneri in the midst of a takeover, they could not compete with Newcastle United for highly rated defender Sven Botman.
The centre-back was said to be a primary target for Maldini, while reports have suggested Paris Saint-Germain have jumped the queue for Botman’s Lille team-mate Renato Sanches.
However, Milan, Maldini and Massara have now come to an agreement that will see two key figures remain in their roles for at least another two seasons.
“This deal highlights the importance of continuity we see throughout the club as we continue to strengthen and grow,” Milan said in a statement.