The prohibition of praying for two things only applies to a congregation, not to individuals (Shulchan Aruch OC 576:15 according to Kaf ha'Chaim ibid. 63). Furthermore, it appears to apply only at times of distress, aqnd perhaps only to specially convened prayer meetings, and not to regular prayers. Hence in every Tefilas Amidah, we request numerous different things. In the last Brachah of Birchas ha'Shachar we request many different things in one Tefilah. Similarly in the Yehi Ratzon of Birchas ha'Chodesh.

The Tefilah in the Kedushah of Yamim Noraim is according to the Mekubalim, so perhaps there is a reason according to the Kabalah that in this specific Tefilah one should not ask for more than one thing. Rav Moshe Sternbuch Shlita writes (Teshuvos v'Hanhagos 2:270) that the Arizal (in Sha'ar ha'Kavanos) explicitly rules out praying for more than one cause at a time in this specific prayer, but he adds that the reasons for this are unknown.

Dov Freedman

I have been unable to find the reference you mention in the Yom Kipur Machzorim that one should not insert more than one personal prayer, and I would be grateful if you could let me know in which Machzor this is cited.

However, my conjecture is that the reason for the above might possibly be nothing to do with our Gemara. The issue here may be a different one. There is a bit of discussion among the commentaries whether on Rosh Hashanah one should make personal requests in the Tefilah. See Kuntres Avodas ha'Tefilah on Rosh Hashanah by Rabbi Mayer Birnbaum Shlita of Passaic, NJ p.36 (in the Hebrew edition) note 40 who cited the Magid Tzedek from which it appears that one should not make any additional requests on Rosh Hashanah, apart from those that Chazal instituted, which are chiefly asking that the whole world should recognize the kingdom of Heaven. On p.37 he cited the Shelah ha'Kadosh who says the same thing. However, in contrast, he also reports that Rav Chaim Kanievsky Shlita wrote in the name of the Chazon Ish that Rosh Hashanah was fixed in order to make any requests that one wants.

Yom Kipur is also the Day of Judgement and the principal Mitzvah of the day is to ask for forgiveness for our sins. Therefore it may be that even according to the commentaries who permit making personal requests on Yom Kipur, nevertheless they also agree that one should try and limit this. This might be the reason that the Machzor says one should only insert one personal prayer.

Kol Tuv,

D. Bloom