Paintings in the 1440s

In 1442, with Medici support, Pope Eugenius IV awarded Lippi an important benefice. A large payment was made in 1447 for St Bernard's Vision of the Virgin (National Gallery, London), produced for the Palazzo della Signoria, as well as final payments for the Coronation of the Virgin, made for Sant'Ambrogio, which was commissioned in 1441.

The Annunciation in the Church of San Lorenzo is among the most successful paintings of Lippi's middle period, with a daring balance of figures, architecture, and landscape. The Annunciation appears to utilize the natural sources within the church itself, which was designed by Filippo Brunelleschi.

Many critics have presumed an interlude during the late 1440s when Fra Filippo was strongly attracted to the painting of Fra Angelico to such a point that a direct collaboration between the two masters has been postulated for the Adoration of the Magi, a tondo rich in detail and incidentals.