After graduating from the seminary in 1883, Bp. Nicholas sent Simeon to the Kiev Theological Academy in Russia for advanced theological studies. There, after passing the oral and written entrance examination, he was enrolled as a student in September 1883. He was the first student from an East Asian country to be enrolled in the Academy, a fact that was widely publicized. In June 1887, he graduated with the high rank of ''Magistrant'', one of only seven in a class of 60. A Magistrant was one step before a Doctor of Theology.

In March 1893, after the couple lost their first-born son Alexander, Simeon chose to enter the [[clergy]]. He was [[ordain]]ed a [[deacon]] by Bp. Nicholas in January 1894, and then a [[priest]] one month later in February. With his high intellectual ability and advanced education, Fr. Simeon rose rapidly. In addition to his clerical duties Fr. Simeon became the publisher-of-record of the new Japanese Orthodox theological journal ''Shinkai'' (Divine Sea), holding this position for the next six years.