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The active war with Spain commenced by the murder of two unarmed Highlanders on Amelia Island, who had gone into the woods for fuel. It was November 14, 1739, that a party of Spaniards landed on the island and skulked in the woods. Francis Brooks, who commanded a scout boat, heard reports of musketry, and at once signaled the fort, when a lieutenant's squad marched out and found the murdered Highlanders with their heads cut off and cruelly mangled. The Spaniards fled with so much precipitation that the squad could not overtake them, though, they pursued rapidly. Immediately Oglethorpe began to collect around him his inadequate forces for the invasion of Florida. In January, 1740, he received orders to make hostile movements against Florida, with the assurance that Admiral Vernon should cooperate with him. Oglethorpe took immediate action, 3rove in the Spanish outposts and invaded Florida, having learned from a deserter that St. Augustine was in want of provisions. South Carolina rendered assistance; and its regiment reached Darien the first of May, where it was joined by Oglethorpe's favorite corps, the Highlanders, ninety strong, commanded by Captain John Mohr Mcintosh and Lieutenant MacKay. They were ordered, accompanied by an Indian force, to proceed by land, at once, to Cowford (afterwards Jacksonville), upon the St. Johns. With four hundred of his regiment, Oglethorpe, on May 3d, left Frederica, in boats, and on the 9th reached the Cowford. The Carolina regiment and the Highlanders having failed to make the expected junction at that point, Oglethorpe, who would brook no delay, immediately proceeded against Fort Diego, which surrendered on the 10th, and garrisoned it with sixty men under Lieutenant Dunbar. With the remainder he returned to the Cowford, and there met the Carolina regiment and Mcintosh's Highlanders. Here Oglethorpe massed nine hundred soldiers and eleven hundred Indians, and marched the whole force against Fort Moosa, which was built of stone, and situated less than two miles from St. Augustine, which the Spaniards evacuated without offering resistance. Having burned the gates, and made three breaches in the walls, Oglethorpe then proceeded to reconnoiter the town and castle. Assisted by some ships of war lying at anchor off St. Augustine bar, he determined to blockade the town. For this purpose he left Colonel Palmer, with ninety-five Highlanders and fifty-two Indians, at Fort Moosa, with instructions to scour the woods and intercept all supplies for the enemy; and, for safety, encamp every night at different places. This was the only party left to guard the land side. The Carolina regiment was sent to occupy a point of land called Point Quartel, about a mile distant from the castle; while he himself with his regiment and the greater part of the Indians embarked in boats, and landed on the Island of Anastatia, where he erected batteries and commenced a bombardment of the town. The operations of the besiegers beginning to relax, the Spanish commander sent a party of six hundred to surprise Colonel Palmer at Fort Moosa. The Spaniards had noted that for. five nights Colonel Palmer had made Fort Moosa his resting place. They came in boats with muffled oars at the dead of night, and landed unheard and undiscovered. The Indians, who were relied on by Palmer, were watching the land side, but never looked towards the water.

Captain Macintosh had remonstrated with Colonel Palmer for remaining at Fort Moosa more than one night, until it produced an alienation between them. The only thing then left for Macintosh was to make his company sleep on their arms. At the first alarm they were in rank, and as the Spanish infantry approached in three columns they were met with a Highland shout. The contest was unequal, and although the Highlanders rallied to the support of Macintosh, their leader, and fought with desperation, yet thirty-six of them fell dead or wounded at the first charge. When Colonel Palmer saw the overwhelming force that assaulted his command, he directed the rangers without the wall to fly ; but, refusing to follow them, he paid the debt of his obstinacy with his blood.

The surprise at Fort Moosa led to the failure of Oglethorpe's expedition. John Mohr Macintosh was a prisoner, and as Oglethorpe had no officer to exchange for him, he was sent to Spain, where he was detained several years — his fate unknown to his family — and when he did return to his family it was with a broken constitution and soon to die, leaving his children to such destiny as might await them, without friends, in the wilds of America, for the one who could assist them — General Oglethorpe — was to be recalled, in preparation to meet the Highland Rising of 1745, when he, too, was doomed to suffer degradation from the duke of Cumberland, and injury to his military reputation.

It was the same regiment of Spaniards that two years later was brought from Cuba to lead in all enterprises that again was destined to meet the remnant of those Highlanders, but both the scene and the result were different. It was in the light of day, and blood and slaughter, but not victory awaited them.