As early as 27 July 1583 Montgomerie was granted a pension by the king, drawn from the revenues of Glasgow Cathedral. His career had evidently survived the temporary imprisonment of James by a militant Protestant faction led by the Earl of Gowrie, and the exile and death of Esmé Stewart, whom James had made Duke of Lennox. But there seems to have been a fundamental change in the culture of the court towards the end of 1585, when the king took personal control of the government, and in the summer of 1586 Montgomerie joined an enlarged Scottish contingent fighting for the Dutch Republic against the Spanish.