As one of the chaplains-in-ordinary to the queen, Overall was appointed by Whitgift in 1598 to preach before her on the third Wednesday of Lent, 15 March, in place of Bishop Godfrey Goldsborough of Gloucester. Shortly afterwards, at Easter, his theological position was further endorsed in Cambridge when he was appointed Master of St Catharine's College, with the support of Whitgift. Thereafter he was occasionally chosen to give Lenten sermons before the queen, but he was not happy in the pulpit. He apparently found it "troublesome to speak English as a continued oration" after years of lecturing in Latin. John Manningham, a Magdalene graduate who would have heard Professor Overall in Cambridge, later complained that he "discoursed verry scholastically" when he preached a Whitehall sermon at the dead queen's court on 6 April 1603