Several days were spent in parleying, for at Cesena Caesar found the envoys of the Vitelli and Orsini, who themselves were with their army in the duchy of Urbino; but after the preliminary discussions as to the right course to follow in carrying on the plan of conquest, there arose such difficulties between the general-in-chief and these agents, that they could not but see the impossibility of getting anything settled by intermediaries, and the urgent necessity of a conference between Caesar and one of the chiefs.

So Oliverotto ran the risk of joining the duke in order to make proposals to him, either to march an Tuscany or to take Sinigaglia, which was the only place in the duchy of Urbino that had not again fallen into Caesar's power.

Caesar's reply was that he did not desire to war upon Tuscany, because the Tuscans were his friends; but that he approved of the lieutenants' plan with regard to Sinigaglia, and therefore was marching towards Fano.
But the daughter of Frederic, the former Duke of Urbino, who held the town of Sinigaglia, and who was called the lady-prefect, because she had married Gian delta Rovere, whom his uncle, Sixtus IV, had made prefect of Rome, judging that it would be impossible to defend herself against the forces the Duke of Valentinais was bringing, left the citadel in the hands of a captain, recommending him to get the best terms he could for the town, and took boat for Venice.
Caesar learned this news at Rimini, through a messenger from Vitelli and the Orsini, who said that the governor of the citadel, though refusing to yield to them, was quite ready to make terms with him, and consequently they would engage to go to the town and finish the business there.

Caesar's reply was that in consequence of this information he was sending some of his troops to Cesena and Imola, for they would be useless to him, as he should now have theirs, which together with the escort he retained would be sufficient, since his only object was the complete pacification of the duchy of Urbino.

He added that this pacification would not be possible if his old friends continued to distrust him, and to discuss through intermediaries alone plans in which their own fortunes were interested as well as his.