The copy of “The Sermon on the Deceased” by Hryhorii Tsamblak, preserved in the library of the Kyiv Cave Monastery, was written in the 16th or early 17th century at the Belarusian Suprasl Monastery. This sermon is a part of the so-called “Hryhorii Tsamblak’s Book,” which may have been compiled by the author himself during his tenure as Kyivan metropolitan. The examined copy of the “The Sermon on the Deceased” and the copy of the same work kept in the scientific library of the Lithuanian Academy of Sciences in Vilnius are of Belarusian origin and differ significantly from the copies created in the Moscow principality. Therefore, it can be assumed that the Kyiv and Vilnius codices originate from a common protograph that was modified either by the author himself or by a scribe in the territory of the Grand Duchy of Lithuania. In “The Sermon on the Deceased,” Hryhorii Tsamblak shares his thoughts on the Christian custom of commemorating the dead. The preacher optimistically proclaims an eschatological perspective for Christians. The didactic purpose of Tsamblak’s sermon is to illuminate the futility of earthly concerns and efforts. The ontological perspective for the righteous pertains to the hope of the resurrection of the dead and eternal life. Based on numerous examples of human activity, such as the hard lives of warriors, farmers, sailors, and ore miners, the preacher attempts to illustrate the concept of “the vanity of vanities” and “the hurricane of human life that passes quickly.” Tsamlak argues that the Christian’s axiology should oppose the cult of enrichment, power, and vanity. Metaphorically and symbolically, he portrays the work of a farmer hoping for a good harvest, which represents the imperishable — eternal life in Christ. “The Sermon on the Deceased” was influenced by the sermons of John Chrysostom and, probably, by one of the works of Macarius the Great. The style of Tsamblak’s sermon can be defined as emotionally expressive.