The Regia Aeronautica (Italian Royal Air Force) was the first to respond. A contingent of Savoia-Marchetti SM.79 Sparviero “Sparrowhawks” and Savoia-Marchetti SM.81 Pipistrello “Bats” were sent into battle from airbases on Rhodes by Rear Admiral Luigi Biancheri and attacked the newly won British positions just hours after the commandos had come ashore. Air bombardments against the gubernatorial castle, the harbor and its surrounding facilities, along with the hillside which the British had concentrated their forces were carried out with positive results. The bombing also inflicted damage to the gunboat HMS Ladybird, which had replaced the destroyers inside the harbor to act as a communications hub for the ground contingent, forcing her withdraw back to safety in Cyprus.
Throughout the battle the Italian’s continued to rapidly press their counter-attack; their speed in reacting, starting from the very first bomber attack on February 25th, seems to stand in contrast to some of the moves and pacing made by the British during the encounter. Late on the 25th, some sources indicate early 26th, the Italians landed a small ‘raider/recon’ party on Castellorizo. The force was made up of soldiers from the 50th Infantry Division Regina. Approximately 65 men of the 201st CN and the 13th/ IV / 9th spent several hours running reconnaissance to gauge the composition and deployment of British strength while also conducting several hit and run attacks. After approximately 5 hours the force re-embarked on to their waiting vessels, and safely departed after the successful endeavor.
The second wave of the British invasion force, anchored by the Sherwood Foresters sailing aboard the boarding vessel HMS Rosaura, was scheduled to arrive on Castellorizo during the early morning hours of the 26th. The soldiers were to be shuttled into Megisti Harbor, mirroring the arrival of the first wave of commandos, to bring needed manpower and supplies. This scheduled landing would not occur however, and the British commandos were denied the reinforcements they desperately required to help hold the island.
The advancing British convoy had received reports from Castellorizo of Italian naval activity north of the harbor. The reports were about the Italian torpedo boats Lupo and Lince, which had first dropped off the recon party mentioned above, and then after moving into range, proceeded to shell British positions from offshore. On receiving these warning, British Rear Admiral Renouf, who was overseeing the operation first hand, canceled the scheduled landing. Possibly unsure of the actual size or composition of the Italian force, Admiral Renouf feared for the vulnerability of the ‘smallish’ Rosaura and the troops she carried. He ordered the convoy to turn around and head to Alexandria in order to transfer the troops onto larger and more heavily armed destroyers for a second attempt the next day. Renouf simultaneously ordered the destroyer Hereward, which had initial sailed away from the island on first reports of enemy naval activity, ahead in an attempt to engage the reported Italian maritime activity. The Hereward was unable to locate her adversaries, and circled back around out to sea empty handed. The British had lost the initiative.
The Italians, on the other hand, were racing forward on the morning of the 27th to begin in earnest the land based portion of their counter-attack. A naval flotilla, led personally by Admiral Biancheri, consisting of the torpedo boats Lupo and Lince, motor launches MAS546 and MAS561, and later in the day bringing heavy firepower, the destroyers Crispi and Sella. The flotilla would, on what proved to be the critical day of the conflict, deliver to Castellorizo nearly 340 soldiers and sailors, most of them hailing from the IV Battalion, 9th Infantry Regiment of the 50th Infantry Division Regina.
The force included about two dozen men from an anti-tank platoon with two 47-mm guns, and a mortar platoon equipped with a pair of 81-mm mortars. The Italians moved inland quickly, gaining ground as they advanced, and pushed the British back, eventually forcing most of the defenders to dig into a small area of the island known as Nifti Point. The Italian ground forces were supported during their advance from the Lupo off shore, which used its 3.9 inch gun to pound enemy positions. A good portion of the Lupo’s fire was directed at Nifti Point and its battered occupants, leading to serious questions of the tenability of this last bastion of British defense.
Later that night (2300) the British once again approached Castellorizo, the Sherwood Foresters having been transferred to the destroyers HMS Decoy and HMS Hero, with the flotilla now filled out with an impressive array of firepower. Joining the troop carrying destroyers were two further destroyers, the Jaguar and Hasty, and the light cruisers Bonaventure and Perth.
The Foresters were disembarked back onto Castellorizo after midnight from their destroyers while the reaming British vessels took up patrols off of Nifti Point. Their stay on the island was not to be long. The commanders for both the commandos and the Foresters appreciated the extreme precariousness of their situation, and the realization of the high probability that without sufficient air support they would not be able to hold their tenuous position on Nifti Point. It was therefore decided a withdrawal from the island was necessary, and within three hours of landing, the troops were evacuated under the cover of darkness back to their waiting vessels. British soldiers would not again set foot on the island for over two more years.
Several of the British commandos, who had either been cut off during the fighting or left behind during the evacuation, were captured by the Italians. Additionally, over two dozen men of the local population were arrested and later convicted of ‘aiding the enemy’, and eventually sent to Brindisi, Italy to serve their sentence. The Italian re-conquest of Castellorizo thus became one of the rare occurrences during World War Two in which Axis forces were able to recapture and hold through force an Island they had previously lost to the Allies. While the fighting on Castellorizo was all but over, out at sea elements of two of the most powerful naval forces on the planet would attempt to strike a ‘parting’ blow during the waning hours of Operation Abstention.