Yesterday being the 30th of Av (and Rosh Chodesh Elul), prompted a question at shul: exactly when do we start saying Psalm 27—on the first day of Elul or the first day of Rosh Chodesh Elul? Most of my siddurim (including ArtScroll) have something ambiguous like "from the start of Elul". The Orthodox Union web site clearly states "beginning with the second day of Rosh Chodesh Elul . . ." On the other hand, Siddur Tehillat Hashem (Chabad) clearly states, "From the first day of Rosh Chodesh Elul . . .". (Just for the record, we included it.)
So is the tradition to have different traditions? What are the authorities for the two opinions?
Answer
With regards to the Chabad tradition of starting from the first day of Rosh Chodesh Elul (which is the 30th of Av), Dayan Raskin (pdf page 217, footnote 469) points toward the Divrei Nechemia's Hashlamot to the Shulchan Aruch Harav 581, Kuntres Acharon 1.
There, the Divrei Nechemia discusses how Moshe's 3rd ascent to Mount Sinai was the first day of Rosh Chodesh Elul, on the 30th of Av. That starts the opportune time period of G-d's willingness to forgive us and accept our repentance (see Divrei Nechemia's 581:1).
The Divrei Nechemia, in 581:2, says that the custom to start blowing Shofar on the first day of Rosh Chodesh is the main one, but those who start on the second should not change their custom, since they have what to rely on. A place without an existing custom however, should start on the first day.
I also vaguely remember once hearing that we learn something out from the number of times (or days) we say L'David, that only works out if you start from the first day of Rosh Chodesh Elul and finish after mincha on Hosha'anah Rabba, but I don't remember the details.
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