The 27th foot, of which his fellow Limerickman General William Blakeney was colonel, was at Porto Bello, with Admiral Vernon, in 1739, and the few survivors returned home in December 1740. Military records show the dates of Massey's commissions in the 27th foot as ensign, 25 January 1741. Massey served with his regiment in Scotland in 1745–1746, and was made captain-lieutenant, and captain in the regiment by the Duke of Cumberland, apparently in 1747, captain 24 May 1751, and major 10 December 1755.