Rabbi Dunner looks at one of the most famous questions ever asked by the Midrash – so famous that it has become colloquially synonymous with randomly connected topics:

מה עניין שמיטה אצל הר סיני, והלא כל המצות נאמרו מסיני – ‘why mention Har Sinai in connection with Shemitta, surely all the mitzvot were said at Sinai?’

In other words, why mention Mount Sinai specifically in connection with the commandment of the Sabbatical year, when every one of the mitzvot in the Torah has its origins at Sinai?

Weaving together Midrash, early commentators, and later commentators, Rabbi Dunner unravels this mystery, and discovers the specific connection between these seemingly unrelated topics.