Ruben Amorim heads into mid-August with four separate situations still hanging over his squad, involving Rafael Leão, Mike Maignan, Adrien Rabiot and Christian Pulisic, according to La Gazzetta dello Sport.
None of these are fringe names, which is what makes the timing awkward. A coach arriving from a difficult spell at Manchester United, backed by Gerry Cardinale to rebuild in Italy, would want clarity on his most important players this close to the season. Instead each case sits on its own separate fault line, personal, tactical and physical.
Leão's future is the one that has dragged on longest. It was late May when the Portuguese forward unsettled the Rossoneri by signalling he wanted to leave, and two and a half months later nothing has moved. He has since said he wants to focus only on football, though only after making his point loudly first.
The problem is the market has not matched his ambitions. No English club has come forward, Turkish sides have made contact but hold no appeal for Leão at this stage, and Milan's stance of accepting nothing below €50m has cooled interest further. So he stays, for now, inside a system that does not obviously suit him.
Early signs suggest the 3-4-2-1 is not Leão's ideal shape. He can adapt, but Amorim would have to bend the structure to accommodate him, which turns a transfer question into a tactical and dressing-room one, with the fanbase watching closely.
Then there are the two Frenchmen. The Maignan and Rabiot situation flared up in recent days, and Amorim played his part by evidently signing off on the request for extra holiday the pair made. It may pass quickly, a penalty saved by Maignan or a goal from Rabiot could settle the mood, but the balance in the group still has to be managed. For Maignan it carries extra weight given he keeps the captain's armband.
The Pulisic case is the most straightforward, because it is purely physical. The American came back injured and is continuing his recovery programme at Milanello, with a return to team training expected on Monday. Starting against Torino looks unlikely. Amorim has been clear that Pulisic is central to his plans in the attacking midfield area, so his place is not in doubt once fit.
From here it falls to Amorim and the club to turn four open questions into settled ones before the season forces the answers.