The first failure to liberate the island of Tilos led the allied administration to the decision to come back with strong forces. The new operation was decided to take place on 27 February 1945. For the new operation strong forces were indeed assembled, with two detachments of the Holy Company, which formed the "Symi Detachment", two companies of the 5th Indian Brigade and the forces of three patrols (12 Hierolochites in total) that were already active in Tilos.
In total, together with the auxiliaries, 513 men, Greeks, Indians and Britons, gathered for the execution of operation "Cave" , as was its code name. From the reconnaissances carried out it was found that the strength of the enemy garrison amounted to 180-190 Germans and some Italians, under the German lieutenant Heinemann who was also the only officer of the garrison.
The bulk of the enemy force was defensively stationed in a line defined by Livadia, Del Fico, 165 and Creati Heights located around the port of Skala Livadia. The defensive site was covered by advanced posts of 6-7 men, which were established on the heights of Mikro Chorio to the west and Lychnos to the south of the site.
The Lychnos outpost, exceptionally, had a strength of 30 men. From time to time, patrols moved towards the area of the bay of Ag. Antoniou, on the northwest coast of the island. The defensive location was reinforced by two 75 mm anti-tank guns. RAK 40, a 37 mm gun. and number of 50 and 81 mm mortars. The Germans also had an armored vehicle with a 20 mm cannon. and a truck, but which could not move, apparently due to lack of fuel.
East of Mikros Hori there was a small airport. The morale of the men in the enemy garrison was low and the defense of the island depended mainly on the personality of Lieutenant Heinemann and a few trusted NCOs. Based on this information, the action plan was drawn up.
The cruiser force would operate in the northern part of the island with two divisions and in the southern part with one division. To the north would act the 3rd Division of the Sacred Company, reinforced by a machine gun platoon, a mortar element and an Indian platoon – 138 men in all – led by Major Demopoulos. This force would land at Zoumboudi Bay, on the northeastern coast of the island.
The second division was made up of the Indian platoon (minus a platoon), a mortar group of the Holy Company, a section of couriers and a medical staff, with a total strength of 246 men, under a British officer, and after landing at St. Antoniou on the northern coasts of the island, it would move towards Skala Livadien, covering from the west the energy of the Dimopoulos section.
In the south would operate the 2nd Division of the Holy Company, reinforced with a machine gun platoon, a mortar element and a squad of two British officers and five hoplites and a total strength of 115 men, under Major Kazakopoulos (Kazakopoulos Detachment). He would land in the bay of Ag. Stergio, on the southern coast of the island. Each of the three forces was attached to the reconnaissance patrols previously sent to Tilos. The command of the raiding force of the Hierolochites was assigned to lieutenant colonel Triantafyllakos.
On February 27 the raiding force boarded the ships, but due to heavy seas the operation was postponed until March 1. In the afternoon of March 1st, the divisions boarded the ships again and sailed from the port of Symi, at 17.00, the Dimopoulos Detachment, at 18.30 the Kazakopoulos Detachment and at 22.00 the rest of the divisions.
Descent to Tilos
The Dimopoulos Detachment landed at 20.00 on the Zoumboudi coast, where it was received by the reconnaissance patrol and informed. Then its head informed his subordinates and defined the missions. The 1st Platoon, under Lieutenant Loumakis, neutralized the enemy outpost at Amali and advanced to the Galata Gremos hill, where it established itself defensively.
Also, the 2nd Platoon established a cut-off on the road to Mikro Chorio, while the 3rd Platoon occupied the Palukotos hill and established itself on hill 265. At the same time, the Indian platoon advanced towards Ag. Antoniou and remained there for the reception of the main force.
The main force landed at the bay of Ag. Antoniou at 02.30 and immediately moved to reinforce the Demopoulos Detachment with one company of Indians towards the Galata Gremos hill and with the other towards hill 265, where the mortar team and the staff of the Holy Company and the 5th Indian Brigade were installed.
The Germans finally realized their opposing divisions and at 04.40, they launched an attack against the Hierolochite division that had occupied the Galata Gremos hill. However, the German attack was easily repulsed. Immediately after, this part of the Holy Company was replaced by the Indian company and moved to hill 265, as a reserve for the Demopoulos Detachment.
By 10.00 the Indian company, after clearing the area south of the Galata Gremos hill, advanced to Mikro Chorio. The Hierolohites section that was on hill 265, advanced to hill 165 – south of the airport – and occupied hill 153 where it established itself defensively. Immediately after, he attacked Hill 165 and by 14.00 he captured it and captured 40 Germans and the commander of the island's garrison.
At the same time, the other company of Indians advanced from the Great Village to the southeast and settled first on the Meravigla hill and then on the Creati hill. The rest of the Hierolohite units of the Dimopoulos Detachment advanced to hill 165, from where they supported with their machine gun fire the advance of the Indian companies from Mikro Chorio and the Kreati hill towards hill 185.
In the southern sector, the Kazakopoulos Detachment landed at 21.30 at the bay of Ag. Stergio from where, with the help of the reconnaissance patrol, it was pushed north and by 00.15 on March 1st it was established on the Gerontes hill. Immediately after, the Hierolochite platoons advanced further north to suitable positions, where they established themselves until 01.30, in order to attack the German outpost defending south of the Vigla hill.
The attack took place at 07.00 of the same day and shortly the enemy's resistance was broken and the 8 men of the outpost guard were captured. The Hierolochites advanced to the Vigla hill, where they established themselves defensively and from where they supported the attack of the Demopoulos Detachment in the area of the Del Fico and Kreati hills. At 08.30 Kazakopoulos' divisions advanced northeast, pressing the Germans in Kastelo and Livadia.
The Germans were forced to retreat to the main site of resistance, but found themselves surrounded. By 16.00, the divisions of Dimopoulos and Kazakopoulos attacked the last enemy resistances of the Livadia defensive location, in conjunction with an Indian company. The objectives were immediately captured and a link was achieved between the sections of the two detachments. At 17.00 the divisions of Dimopoulos and Kazakopoulos attacked the organized enemy location, with the assistance of the naval gunners covering the operation.
In this way, in a short time the area of Livadia was cleared and all the defenders were captured. At the same time, a group of Hierolohites of the Kazakopoulos Detachment occupied the Kastelo hill and captured the 8 Germans of its guard. By 18.00, the enemy garrison of the island had been completely neutralized and the units of the commando force were ordered to gather in the Livadia area, where they would spend the night, advancing outposts on the heights of Del Fico and Gerontas.
The raiding force remained on Tilos until March 2 and immediately departed, leaving a patrol of 5 Hierolochites to control the island. German losses during the "Cave" operation reached 20 dead and 142 prisoners, of which 8 were wounded. All the artillery and heavy weapons of the garrison were taken over. The losses of the raiding force were two Indians dead and two Hierolohites wounded.