Prototype

You will need to infiltrate a military base in the mission "The Wheels of Chance" and so the game will teach you how to do so. After you know how and have completed the mission, simply repeat what you did in the mission at nine other bases to unlock this trophy. It will be beneficial to you do to so as not only will you work towards the trophy, but inside the bases will be other military personnel you can consume to upgrade your skills with weapons and military vehicles, along with some Web of Intrigue targets.

You can track your progress under the Statistics -> Military page on the pause menu