From 1606 to 1608 on the side of the Tsar Vasily Shuisky he took part of the battles against Bolotnikovites, Polish-Lithuanian invaders and supporters of False Dmitry II. In 1606 Prince Trubetsky was the first voivode of the guard regiment in the tsarist army under the command of the Princes Fyodor Ivanovich Mstislavsky and Mikhail Fyodorovich Kashin-Obolensky under Serpukhov. In autumn of the same 1606 the Tsar Vasily Shuisky sent an army of three regiments to the punitive campaign against the rebellious Severia. The big regiment was led by Prince Trubetsky, and boyar Mikhail Alexandrovich Nagoy, forward regiment by the Princes Boris Mikhailovich Lykov-Obolensky and Yakov Petrovich Baryatinsky, the guard regiment by the Princes Grigory Petrovich Romodanovsky and Roman Ivanovich Gagarin. In the Battle of Kromy the tsarist army was defeated by the rebel army under the command of Ivan Isaevich Bolotnikov and Yuri Bezzubtsev. The chief governors, Trubetsky and boyar Mikhail Alexandrovich Nagoy, with the remnants of the regiments retreated to Oryol, and from there to Moscow.
