In the summer of 1902, a student at the Ecclesiastical Academy named Leonid Feodorov approached Archimandrite Theophan seeking permission to interrupt his studies for the priesthood and be granted a passport for a foreign trip to Rome.

Cyril Korolevsky alleges that Archimandrite Theophan, "was quite convinced of the truth of Catholicism, but like a number of others he could not bring himself to take the definite step.

In 1908 Theophan (and brother Makary) visited Rasputin in his home village Pokrovskoye and investigated his supposed Khlyst behavior, after charges made the year before.

Theophan was a devout monarchist and came to the conclusion Rasputin was a garrulous person, a false starets and could be a danger to the throne.

He was appointed bishop of the eparchy of Simferopol and at the same time elected as an honorary member of the St Petersburg Theological Academy.

Despite his many desperate efforts to expose Rasputin's manipulative nature to the last Tsar and Empress, Theofan was unable to forgive himself for having introduced his former protege to the Imperial family.

Blaming himself for the overthrow of the House of Romanov, the October Revolution, and the subsequent Red Terror, Theofan spent many nights lying prostrate before the altar of St. Alexander Nevsky Cathedral in Sofia, "wailing about his guilt" and imploring God's forgiveness.