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For almost three hundred years the monastery was an important outpost of the Russian nation, defending its western border against attack from the west. The area was involved in almost constant warfare during these centuries. It was attacked by Livonians for years following its founding in the late fifteenth century. In 1581-1582, the monastery was under siege by the Polish king Stefan Batory. During the Time of Troubles, between 1611 and 1616, the monastery was attacked by Polish and Swedish forces. But, after the Tsar Peter I’s wars of 1700 to 1721, the monastery lost its importance and lapsed into relative obscurity.
During the middle of the sixteenth century Pskov-Caves monastery rose to its greatest level of prominence under the leadership of St. [[Corneliusof the Pskov Caves|Cornelius]], [[abbot]] of the Pskov Caves. In 1529, the monk Cornelius became an [[igumen]] and abbot of the monastery, at the age of twenty-eight. In addition to expanding the intellectual and spiritual efforts of the monastery, that included missionary work, the Pskov chronicles, and books that he wrote, he sponsored many physical changes to the monastery. He enlarged the monastery caves, moved older churches, built the Church of the Annunciation of the Most Holy Theotokos in 1541, and the Church of the Protection of the Most Holy Theotokos in 1559. Between 1558 and 1565, St Cornelius had the stone wall built around the monastery including a stone church dedicated to St. Nicholas over the gates of the monastery. He also encourage the preaching of Christianity to the pagans in the occupied cities of the area during the Livonian wars. During his tenure as abbot the monastic population of the monastery increased from 15 to 200, a number that has not been surpassed since.
[[Image:PskovCavesBloodyPath9Apr2009.JPG|left|thumb|250px|The “Bloody Path” from St Nicholas Gate of the monastery]]
Even in his death, St. Cornelius left his mark on the monastery. On [[February 20]], 1570, Tsar [[Ivan IV of Russia|Ivan IV]] (the terrible), arrived at the Pskov Monastery in a raging anger over a false slander. St. Cornelius met him with a cross at the monastery gates, where upon Ivan attacked the sainted abbot, beheading Cornelius with his own hands. Ivan immediately became remorseful and repented his deed. Ivan then picked up Cornelius’ body and carried it down the path from the gates to the Dormition Cathedral, making a pathway scarlet with the Saint’s blood, a pathway that became known as the ''Bloody Path''.
