Giacomo is appointed castellan of the fortress of Ravaldino in place of his brother, and is awarded with an order of chivalry from Ludovico il Moro.

All the contemporary chronicles report that Caterina is madly in love with the young Giacomo.

It is feared that she could strip her son Ottaviano of his future lordship, in order to give it to her lover and secret husband.

In April 1489, Caterina gives birth to Giacomo's son, Bernardino, later called Carlo in honor of King Charles VIII, who had made Giacomo a baron of France.

Also, she had replaced the castellans of the fortresses of her dominions with her closest relatives: the fortress of Imola has been given to Gian Piero Landriani, her stepfather, and the fortress of Forlimpopoli to Piero Landriani, her half-brother, while Tommaso Feo is married to Bianca Landriani, Caterina's half-sister.

At Tossignano, a conspiracy is formed to seize the fortress in the name of Ottaviano, and murder both Giacomo and Caterina.

The Countess discovers the plot and imprisons or executes those who are involved.

Immediately after this conspiracy is foiled, another plot is organized by Antonio Maria Ordelaffi, who had never become resigned to the loss of Forlí, but this also fails.