From 1783 to 1787 he served in the West Indies. In 1787 he was master"s mate in the Sirius when the First Fleet sailed for Australia. Shortland spent nearly five years in Australia including time on Norfolk Island where Sirius was wrecked in 1790.
In 1792 he returned to England.
While Shortland was in Egypt, he flew a kite over Pompey"s Pillar. This enabled him to get ropes over it, and then a rope ladder.
Then on 3 February 1803 he and John White, Pandour"s Master, climbed lieutenant When they got to the top they displayed the Union Jack, drank a toast to King George III, and gave three cheers.
Three days later they climbed the pillar again, erected a staff, fixed a weather vane, ate a beef steak, and again toasted the king.
On Shortland"s return from Egypt in 1803, he paid off Pandour. A few days later he was appointed to Dolphin, also a troopship. After serving briefly on her, he transferred to the 18-gun sloop Trompeuse.
On 13 December 1809 he was captain of Junon when it engaged and was overwhelmed by two 48-gun and two 20-gun French ships.
Shortland was very seriously wounded and his ship so badly damaged that the enemy was compelled to burn her. He was buried with full military honours at Basse-Terre.