The monastery was founded in the 1370s by Vladimir the Bold and long served as a border fortress defending the southern approaches to Moscow from the Tatars.
In the mid-17th century the monastery was fortified with stone walls and four corner towers. It rivalled the Vladychny Monastery as the most important shrine of Serpukhov and welcomed rich patrons wishing to be buried within the monastery walls. Among those buried there are Gavrila Golovkin, the Chancellor of Peter the Great, and Fyodor Soimonov, the Governor of Siberia. The Neoclassical belfry was completed in the 1840s.
The monastery celebrated its 500th anniversary with the construction of the All Saints church, designed by Roman Klein in a fashionable Neo-Byzantine style.
The modern monastery derives its prosperity from the venerated copy of the icon of the Inexhaustible Chalice, which attracts hundreds of pilgrims from all over Russia and abroad. The icon was brought to the monastery from the Vladychny Convent (also in Serpukhov) and is said to be particularly effective in the treatment of alcoholism.