Troubridge was born into a family with substantial military connections, with several of his forebears being distinguished naval officers. He too embarked on a career in the navy, rising through the ranks during the late Victorian period, and commanding ships in the Mediterranean. He served as a naval attaché to several powers, including the Empire of Japan during the Russo-Japanese War. He spent some time immediately before the outbreak of the First World War as a staff officer and assisted in the drawing up of strategic plans to be adopted in the event of war, though these were later rejected. He returned to seagoing service just prior to the outbreak of war, and commanded a cruiser squadron in the Mediterranean with the rank of rear-admiral. Here his promising career was blighted by the events surrounding the pursuit of two German warships, and . Despite being outclassed by the German warships, Troubridge intended to engage them, but was convinced otherwise by his flag captain and allowed them to escape to Constantinople. He and his commanding officer were heavily criticised for their failure to intercept the German ships, particularly when it subsequently appeared that they became influential in the Turkish decision to enter the war. Troubridge was court-martialled and although he was acquitted, his reputation had been damaged.