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Today, the month of Elul is seen as being an introduction to the period of the High Holy Days (Rosh HaShanah and Yom Kippur).

For instance, Tur Orach Chaim 581:

התקינו חז"ל שיהו תוקעין בר"ח אלול בכל שנה ושנה וכל החדש כדי להזהיר ישראל שיעשו תשובה ... ויש מי שמרבין לומר סליחות ותחנונים מר"ח אלול ואילך

Our Sages instituted that we sound the shofar on Rosh Chodesh Elul every year and throughout the month to warn Israel to repent ... And there are those that increase the recitation of penitential prayers from Rosh Chodesh Elul and onwards.

I am unaware of any Talmudic source that makes this connection. Where do we first see a link made between Elul and repenting in advance of the High Holy Days?

The earliest source I see so far is a quote from R. Isaac ibn Ghiyyat (רי"ץ גיאת) who lived in the mid-11th century. He is quoted by Rosh on Rosh HaShanah 4:14 as writing:

אמר לי רב כהן צדק מנהג בשתי ישיבות לומר תחנונים בהני עשרה יומי שבין ר"ה ליום הכפורים וכן אומר רב עמרם ורב האי מנהג לומר תחנונים בהני עשרה ימים בלחוד ושמעינן דמקצת אתרוותא קיימי מראש חודש אלול

R. Cohen Tzedek said that the custom in the two yeshivot [Sura and Pumbedita] is to recite penitentiary prayers during those ten days between Rosh HaShanah and Yom Kippur. Similarly, R. Amram and R. Hai said that the custom is to recite penitentiary prayers during those ten days only. And I have heard that in some places they have them from Rosh Chodesh Elul.

I know that Pirkei de-Rabbi Eliezer 46 discusses a custom of blowing the shofar, but it seems to be only on Rosh Chodesh Elul, and is connected to Moshe ascending Har Sinai for the final time, rather than explicitly as a call to repentance.

Conversely, one could argue that the ancient custom to recite haftarot of comfort (שבע דנחמתא) throughout Elul and only afterwards to recite two hafatarot of repentance (תרתי דתיובתא) indicates that Elul was seen more in its relation to the fast of Tish'ah BeAv that preceded it, rather than to Rosh HaShanah and Yom Kippur. This custom is quoted in Tur Orach Chaim 428, referencing Pesikta de-Rav Kahana, which is (or at least contains a core that is) an Israeli midrash dating to around the fifth or sixth centuries.

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The earliest source I'm aware of is from the second year of Darius. See Haggai, chapter 1.

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  • Nice source. Although this prophecy is not explicitly connected to the time of year, nor repentance in general (it seems rather to be a rebuke for not rebuilding the Beit HaMikdash). Are you aware of any commentaries that tie this chapter into the theme of Elul as it's currently practiced?
    – Joel K
    Aug 16, 2018 at 12:35
  • It is explicitly in that time of year and explicitly about repentance! שימו לבבכם על דרכיכם Literally a Teshuva Drasha on Rosh Chodesh Elul! Any exhortation to repent will focus on whatever sins are problematic at the time, and Chaggai too is seemingly Nevuah Ledorot. Yes, Kaf Hachayim recommends reading Chaggai on rosh chodesh elul
    – Double AA ♦
    Aug 16, 2018 at 12:36
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    By the same token, Marcheshvan should be seen as a time of repentance. See Zechariah 1. I'm not convinced of the fact that a specific prophecy occurred on a specific date teaches us all that much about that time of year (without further sources that indicate that).
    – Joel K
    Aug 16, 2018 at 12:46
  • Note that the actual body of the question was, "Where do we first see a link made between Elul and repenting in advance of the High Holy Days?" I don't really see that in Chaggai.
    – Joel K
    Aug 16, 2018 at 12:47
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    The parsha break before 1:15 instead of before 2:1 where you would expect it might be a hint to the link between Elul and Tishrei in particular. (And also maybe between the Yamim Noraim and Hoshana Rabba.) @JoelK
    – Heshy
    Aug 16, 2018 at 17:14

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