The aim of this article is to reattribute to the painter Baldassarre Carrari (Forlì, c. 1460-1516) two paintings, both characterized by a sophisticated iconographic program. The first is a 'Blessing Christ Carrying the Cross', datable to around 1510 on account of its close stylistic affinity with the 'Deposition' in the Pinacoteca of Forlì. In the panel here attributed to him, the influence of Rondinelli is particularly evident: the painting displays a more fluid and unified handling than in his earlier works, with greater attention to the psychological rendering of the face and a heightened sensitivity to atmospheric effects. The iconography of Christ Carrying the Cross, imbued with a powerful devotional charge, enjoyed wide diffusion in Romagna in the early sixteenth century. Yet the variant under examination here – namely, the addition of the blessing gesture – is entirely unprecedented, demonstrating how Carrari and his patrons distinguished themselves within the artistic context of Romagna through the adoption of highly unusual solutions. The other painting here attributed to the artist, a 'Virgin and Child with Eve', likewise displays these distinctive features. Datable to the later phase of the painter's activity, given its explicit homage to the manner of Rondinelli – to whom the work had hitherto been attributed – the painting is also notable for the presence of original verses in a Dantean style inscribed within the composition. The juxtaposition of Eve and Mary – the only two women in Christianity born without original sin – refers to a debate that, particularly from the pontificate of Sixtus IV onward, became especially fervent in Romagna at the turn of the sixteenth century: namely, the question of the Immaculate Conception, which, as is well known, would become a dogma only in the nineteenth century. In the iconographic reading of the painting, the Virgin is presented as having come to free humanity from the sin brought about by Eve.