Well, I know from playing Paradox strategy games that Urbino was a vassal of the Papal State, so it’s tricky to conquer it without pissing off the Pope and then getting yourself excommunicated :)
Are you hungry or thirsty? Supposedly what the Lord of Milan and complete scoundrel Bernabo Visconti said to the Pope’s messengers on the middle of a bridge. He’d been an on again off again papal supporter and now they were on the outs and this was a tough love message from the sort of a scoundrel himself big guy. He read it and without giving any other reaction asked the question. They said hungry and Bernabo ordered them to eat the scrolls leather straps and all. Apparently if they said thirsty he would have thrown them in the river which they probably wouldn’t have survived. So they chose wisely. I love history.