In 1596 the Earl of Tyrone, after having pretended to submit to the Government, made an incursion into the Pale. It seems that his foremost troops were commanded by his son-in-law, Henry Oge, who endeavoured to surprise the castle at Carlingford. This he was unable to accomplish, but, “missing of his principal purpose, there were carried away as prisoners, in lamentable manner, two gentlewomen, daughters of Captain Henshaw, the one married and the other a maid.” The Earl, who was following, had intended to reinforce the troops after the seizing of the town and fortress, but the failure of the enterprise prevented his doing so. He acknowledged having carried off the ladies from the castle “in time of peace,” and refused to return them until O’Hanlon’s son was liberated in exchange. Marmaduke Whitechurch was constable of Carlingford in 1610, and had six warders under his command. In 1641 “Sir Con Maginse tooke the forte and castle of the Neurie and Carlingfoorde.” The next year it was captured by a ruse graphically described as follows: “5th of May. Newes came from Dundalk to the Lords Justices by Captaine Cadogan (who came thence through Maday with ten horse-men only) that the Newry was not only retaken by the Lord Conway and Munroe, the Scots commander, from the rebels, but also that the towne and castle of Carlingford were taken by a ship that came from Knockfergus. Their policy was to put up the Spanish colours, which the rebels discerning, sent a fisher-boat, with ten or twelve of their commanders, to goe aboard the ship, supposing that some ammunition was come unto them; but the captaine of the ships, instead of shewing them any such commodities, clapt them up under decks, and so landing his musketiers, they took the towne, which they of the castle soone perceiving, fled away, and left both unto our forces.” In 1648 Lord Inchiquin marched on Carlingford after capturing Dundalk, and seems to have had little difficulty in getting possession of the town and fortress. The following year Colonel Venables appeared before the walls with Parliamentary forces. Upon his making preparation for the landing of cannon the town and castles were surrendered. In a letter to Oliver Cromwell he speaks with great praise of Captain Ferns, who “came to the harbour’s mouth with his fregot, and upon a signal agreed between us, came gallantly in under fire,” although his mainmast was split by a shot from the castle. He captured a small Wexford vessel then in the bay. Carlingford was no mean prize, as it formed the chief storehouse of their opponents’ arms in Ulster. The three castles and the sea-fort contained in all seven pieces of ordnance, nearly 40 barrels of powder and the same of small shot, over a thousand muskets, and 480 pikes. They did not find much provision in the town. The next day Newry surrendered. The fortress must have been subjected to bombardment at some time, as cannon-balls have been found among the ruins.