In 1281 he was with the Guelphs of Siena who were besieging their Ghibelline fellow citizens in the Torri di Maremma, near Roccastrada, Tuscany, and he was fined many times for deserting the battlefield without permission.
We can deduce from Sonnet 102 (from 1302 to 1303), addressed to Dante who was already in Verona, that during this period, Cecco was in Rome ("s'eo fatto romano, e tu lombardo").
In 1302 Cecco had to sell off his vineyard to one Neri Perini del Popolo di Sant'Andrea for seven-hundred lire, and this is the last information that is available from Angiolieri's lifetime.
From a later document (25 February 1313) we know that five of his children (Meo, Deo, Angioliero, Arbolina and Sinione- another daughter, Tessa, had already left the household) renounced their inheritance because the estate was too far in debt.
Even in those poems which seem most personal we find a taste for parody and caricature, and stylistic exaggeration, in which emotions and passions are the pretext for linguistic games.