James Cunningham arrived in NSW aboard HMS Sirius as Ship’s Master’s Mate in 1788. He arrived on Norfolk Island aboard HM Supply in Mar 1788.
He drowned on 6 Aug 1788 whilst on way out to HM Supply on her return journey to Norfolk Island the boat he was in was swamped and he lost his life along with three others – John Williams and Laurence Tomlinson, William Westbrook.
26th August. The Supply arrived from Norfolk Island, after a long and rough passage. She had landed, but neither in apparent safety nor with facility, the stores which she carried to that place: and, upon the present occasion, I am sorry to add, that the hazard of landing and embarking from this little island is so very great that Mr. Cunningham, a midshipman of the Sirius (who resided on it with Lieutenant King, the superintendent), was lost, with three seamen, in a boat that was swamped by the surf, which on every part of the coast runs high, and beats against the shore with great violence; so that I much fear, from the difficulty of access, and its situation, it never will prove of any great consequence, although it promised some advantages, particularly in furnishing us with pine trees, which grow here to a size nearly equal to those of Norway. 
On the 26th the _Supply_ returned from Norfolk Island, having been absent five weeks and two days. .. the landing was found to be very dangerous, and he had the misfortune to lose Mr. Cunningham, the midshipman, with three people, and the boat they were in, by the surf on the reef, a few days before the _Supply _sailed. Short, however, as the time was, the carpenter of chat vessel replaced the boat by building him a coble of the timber of the island, constructed purposely for going without the reef, and for the hazardous employ she must often be engaged in.
2nd October: The same day the Golden Grove sailed for Norfolk Island, with a reinforcement of male and female convicts; two free men, as gardeners; a midshipman from the Sirius to fill up the vacancy occasioned by the death of Mr. Cunningham; a sergeant, corporal, and six privates; and a supply of necessaries for eighteen months. 
GOVERNOR PHILLIP TO LORD SYDNEY.
(Despatch No. 7, per H.M. Ship Sirius to the Cape of Good Hope; acknowledged by Rt. Hon. W. W. Grepville, 19th June, 1789.)
Sydney Cove, Port Jackson
My Lord, 28th September, 1788.
Extracts from my letters by the ships which sailed in July accompany this letter, and I have now the honor of informing your Lordship that the Supply sailed for Norfolk Island the 17th of July, and returning the 26th of August, brought me the following particulars from the Commandant of that island. He says that immediately after being landed they proceeded to clear ground sufficient for building huts for themselves and a storehouse, the whole island not affording a single acre free from timber. They were landed on the south-west end of the island, a rough sketch of which I received from that officer, and have the honor of enclosing your Lordship. The bay in which they landed is sheltered by a reef of coral rock, through which there is a passage for a boat, but which, with the tide of flood when the wind is westerly, makes the landing dangerous; and a midshipman who was ordered to lay within the reef, in order to attend the boats coming on shore, imprudently letting the boat drive into the surf, was lost with four men. This was the second time the boat had been overset with that midshipman in her, and the first time one man was lost.
Image: Monument for First Landing Party site March 1788, Kingston Norfolk Island
- Norfolk Island History Lovers Tour
- Norfolk Island first landing party March 1788
- Births and Deaths Norfolk Island 1788 to late January 1791
- Deaths and Burials Norfolk Island 1788 – 1814
- First Fleeters deaths on Norfolk Island
- First Fleeters Deaths 1788 Sydney and Norfolk Island
 John White, Account of a First Fleet voyage to New South Wales, and descriptions of animals, birds and plants, p. 211 – 212.
 David Collins, An Account of the English Colony in New South Wales, Volume 1.
 White, op. cit., p. 214.
 HRA, Series 1, volume 1, p. 70.