For this trophy you have to select a mission at the terminal for the special operations and most importantly, you have to set the level of difficulty to at least master 1. As soon as you are in the mission, lola will inform you that you should free some of their guerrillios. this is a side mission. On each of the missions there are 3 areas where you can find the guerrillios. The position is marked each time with a pink flare that you can see in the air. When freeing it is important to kill the special units quickly, otherwise the hostages will be shot. After the 3 hostages have been freed, the side mission is completed. Lola will give you a quick call. then you can go to the options and choose restart in system tab. The whole thing should not take longer than 5 minutes. Repeat the process 10 times in the best case and the trophy is yours.