He then spent much of the next years in England, and after James V died following the Battle of Solway Moss, Hepburn signed a pact with Henry VIII promising to serve him and aid the commitment of the then infant Mary, Queen of Scots, into Henry's custody.

It was said that Hepburn believed there was the possibility of marrying into royalty and that was his reason for divorcing his wife.

However, the prospects for royal marriage were thin and despite Henry VIII engaging in another bloody invasion of Scotland, Hepburn resumed correspondence with the English Court.

[citation needed] In the intervening years, Hepburn apprehended George Wishart in January 1546, who was put on trial for heresy and executed at St Andrews on 1 March 1546.

In 1548, Hepburn renounced his loyalty to the Scottish crown, and became a pensioner of England, earning £3,000 annually.