The yomim tovim are not merely ?holidays?, i.e. times to break from the routine of daily life and celebrate some past event, group of people, or societal institution. Rather, each yom tov is distinctively, intrinsically holy, and it is the unique kedushas ha-yom of each yom tov which generates the mitzvos which Hakadosh Baruch Hu commands us to keep that day. Each yom tov, if properly appreciated and taken advantage of, can be a time of unique spiritual growth. The exceptional nature of yomim tovim is perhaps most obvious and pronounced during the Yamim Noraim and in their aftermath, on Sukkos. This volume collects nineteen years (1999-2017) of divrei Torah that provide insight and guidance regarding the obligations and opportunities that we each have every Elul and Tishrei. We hope that making them available in a sefer will, b?ezras Hashem, help each of us take maximal advantage of the unique opportunities intrinsic to the Yomim Noraim and Sukkos. The divrei Torah contained herein were originally written by our rebbeim for TorahWeb.org. The realities of the time pressures with which these Torah leaders function on a daily basis result in the divrei Torah on the web site often not being properly edited, missing mareh mekomos, etc. These shortcomings were addressed for the version of the divrei Torah included in this volume. The TorahWeb Foundation, a 501(c)(3) not-for-profit organization, was founded in 1999 at the initiative of members of our community. Its goal is to disseminate divrei Torah and hashkafa, with special attention to contemporary religious and social issues. TorahWeb?s board consists of Rav Hershel Schachter, Rav Michael Rosensweig, Rav Mayer Twersky, and Rav Mordechai Willig. TorahWeb?s primary projects have been publishing weekly divrei Torah written by our rebbeim on www.TorahWeb.org as well as on our email list and arranging for leilei iyun a number of times a year in various communities, the audio and video of which is available on TorahWeb.org as well. Neither the rebbeim nor other individuals involved in TorahWeb receive any financial compensation. In addition, shuls receive the leil iyun programming free of charge. Please send any suggestions, comments, or questions to TorahWeb@TorahWeb.org.