Was sent to Port Arthur, Manchuria, a naval base for the Russian Far Eastern fleet. Accompanied by his wife, he was provided with an enormous bank account, the funds from which he purchased an interest in a small timber company as well as a Danish company (for whom he served as a manager). In reality, these were covers for his real business, spying on the Russian naval assets in Port Arthur. Reilly observed and recorded the positions and schedules of Russian warships as well as assessments of their armaments, crews and capabilities. He even drew sketches of the ships and the port. Reilly sent this information back to England, but was believed by some to have also had financial dealings with Russian and Japanese intelligence officers.

Was brought into the Secret intelligence Service (later known as MI6) in 1909 and served under Captain Mansfield Smith-Cumming. While SIS and NID were pleased with Reilly's capabilities and results, Smith-Cumming said of Reilly "[H}e is a man of indomitable courage, a genius as an agent, but a sinister man who I could never bring myself wholly to trust."

Was sent to Essen, Germany in 1909 to monitor the vast growth of the German war machine. He devised a cover as a Baltic shipyard worker named Karl Khan secured a job as a welder in a Krupp armaments plant. His plan was the photograph the plant and its production output, but he realized that the drawing office was heavily guarded during the day. Instead he volunteered for the fire brigade which worked during the night shift. A few nights later, he strangled the head of the night security detail and incapacitated another security officer, thereby gaining access to the drawing room. In true Reilly fashion, rather than bothering with photographing the plans, he simply stole them, hopped a train and then a boat and evaded German agents as he escaped back to England.

With England still interested in Germany's naval and military capabilities, Reilly was sent to Russia where he pose as an armament distributor. Believing that aerial reconnaissance would provide the best opportunity for seeing and assessing the strength of the German fleet, he used his burgeoning bank account to sponsor air races for Russian aviators. In addition to establishing him as a member of the social elite, it also enabled him cover for flying over areas of the Baltic Sea, photographic German vessels. Through his newfound social connections, Reilly was introduced toa man named Massino, the assistant to the Russian Minister of Marine. Reilly seduced Massino's wife, Nadine, who confided that a German company, Blohm & Voss, were seeking to win the contracts to rebuild the Russian fleet. Reilly bought a small company (Mendrochovich & Lubersky) and pursuaded Massino to convince Blohm & Voss to name his company as their St. Petersburg agents. After Blohm& Vos was awardrd the contracts to rebuild the Russian fleet, they sent copies of all of their designs to Reilly's firm, the designs having been based on the German fleet. Before he turned the plans over to the Russian Minister of Marine, he made a full set of photographic copies, which he sent back to England.

Was able to reach an agreement with SIS so that any profits he earned through his "cover" businesses were kept by him. Reilly became very wealthy through his SIS funded endeavors.

Enjoying Russia, he stayed, living a life of luxury and social prominence. He purchased a small palace where he entertained Nadine Massino and a bevy of other beautiful women. Eventually he planted stories in Russian newspapers claiming his wife Margaret had died in a train crash. He then paid Massino a large sum of money to divorce Nadine, whom Reilly eventually married in New York City in 1916.

Was engaged by Russia to purchase arms for its war effort. Reilly purchased arms from the United States and from Japan.

Was asigned a new mission at the behest of British Prime Minister David Lloyd George. With the Russian government in tatters (after the overthrow of Czar Nicholas) Alexander Kerensky had taken control of the government as the new Prime Minister and was struggling to keep Russian in the fight of World War I. Ultimately, the Bolsheviks overthrew the Russian government and under the revolution's leader Vladimir Lenin, signed a peace treaty with the Germans in 1918. Reilly, in cooperation with Robert Bruce Lockhart, the British general counsel to Russia, attempted to overthrow the new Russian (Bolshevik) government in order to bring Russia back into the war.

Was assigned to a new mission for England, sent to Germany again, this time to assess German army strength and movements. Speaking German fluently, he actually joined the German army and served on the Western front, while sending detailed assessments of German troop plans back to England via carrier pigeons.

Claimed to have impersonated the Chief of Staff to Rupert of Bavaria, thereby gaining access to planning conferences of the German high command, information of great importance that he passed back to London.

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