In this article, we have tried to consider the only image of Theotokos from church No. 16 among all frescoes found in Chersonesos in the context of the intended purpose and status of this church by analogy with the painting program for conformable sacred buildings. At first glance, the preserved fragment of the Blessed Virgin figure is too small to give any information about the typology of Her image. The Blessed Virgin is depicted from the front though this feature is specific to many iconographic types of Her, so the circle of search is too large. Nevertheless, the holdings of the State Museum-Preserve “Tauric Chersonese” still keep one that has not been previously published. It is a fresco fragment from the apse of church No. 16 with the image of the left hand with an open palm and outstretched fingers. This significantly narrows the search space, since the hands and face of the Virgin Mary are portrayed in the manner described above in only two cases: these are images of Orans and “Znamenie”. Both are found in apses and can act equally well as analogues. The construction period of church No. 16 is dated from IX - XI centuries to the XIII - XIV centuries, which coincides with the appearance of tradition in Byzantine monumental painting to put images of Orans in the apses. For the first time ever, such painting program commences to come true in the second half of the IX century, and becomes canonical for the XI - XII centuries. But when exactly does the long-sought image appear and is it spread in the Crimean territory? We did not manage to find clear cogent direct analogies among the local monumental paintings. That, of course, primarily explained the very low preservation of the latter, and in the future it requires the involvement of other types of sources.