Cunningham joined HMS Sirius on 6 Nov 1786 at Deptford, crew number 110. Cunningham was promoted to master’s mate on 29 Sep 1789. He arrived on Norfolk Island per HMAT Supply Mar 1788.

He drowned 6 Aug 1788 whilst on return trip from HMAT Supply to shore, the boat was swamped and he lost his life along with three others: John Williams, Laurence Tomlinson (able seaman HMAT Supply) and William Westbrook. Philip Gidley King noted in his journal the surf was dangerous and a flowing tide, the surge broke into the boat and overset her … the boat drove out to sea and was lost.