In November 1542, he was taken prisoner by the English at the Battle of Solway Moss, but released at a ransom of 1,000 marks, paid on 1 July 1548.
During the Regency of the Earl of Arran he took messages from Mary of Guise to the English ambassador Ralph Sadler.
[2] Fleming's principal house was Boghall at Biggar, where he founded the collegiate church in 1545.
[3] Malcolm married Janet Stewart, illegitimate daughter of King James IV of Scotland, after being granted a dispensation on 26 February 1524/5.
His will included £50 owed to him by Mary of Guise, and in it he wished to be buried in his new church and his father's remains to be taken there from Boghall.