In 1454 the Sienese painter Francesco di Bartolomeo Alfei faced litigation from the Mercanzia in Siena for defaulting on a contract from one of the leading Franciscan confraternities in the city. Two fellow Sienese artists, Giovanni di Paolo and Sano di Pietro, had recently completed a new altarpiece for the same entity. Anabel Thomas considers how the two commissions were linked and questions why Francesco di Bartolomeo Alfei's brief to fresco the confraternity chapel remained unfinished.In a wide ranging analysis of mainly unpublished records, focussing on the artist's association with key members of Sienese society, fellow artisans and government officials, Thomas concludes that Francesco di Bartolomeo Alfei might have honoured his contract had he not become immersed in the military strategy, diplomacy and visual propaganda of the Republic of Siena.