Answer: Beginning from tonight, the Seventh of Marcheshvan, the Jews in Israel begin requesting rain within the Amida prayer within the “Barech Alenu” blessing. If one has completed the Amida prayer without requesting rain (by reciting “Ve’Ten Tal U’Matar Livracha”), one must repeat the entire Amida. If one is unsure whether or not he has requested rain in the Amida prayer, if this occurs within thirty days of beginning to request rain, we must assume that he did not do so and one must repeat the Amida prayer. However, if this occurs after thirty days, one need not repeat the Amida prayer, for we may assume that he has already become accustomed to the change in the prayer.
We must now discuss whether one has the option of accustoming himself to asking for rain such that if an uncertainty rises as to whether or not he has requested rain, he will be able to assume that he has requested rain and his law will be similar to one who is unsure after thirty days from the date of change have elapsed in which case he will need not repeat the Amida.
A Precarious Ox
The Gemara in Masechet Baba Kama (24a) discusses the law of a “precarious ox” which is an ox that gored three times (whose owner must guard it more carefully than a regular ox; payment for the damages inflicted by such an ox varies from that of a regular ox). If an ox gores three times within a prolonged amount of time between each goring, the ox is considered “dangerous.” The Gemara deduces that certainly if the ox gores three times with each goring right after the next that the ox is considered “dangerous,” for this is an indication that the ox is more inclined to gore and the owner must therefore safeguard it well.
The Opinion of Maharam of Rottenberg
Maharam of Rottenberg compares this law to ours and rules that if the Sages established that one who prays for thirty days while requesting rain in the “Blessing of the Years” is already assumed to have accustomed his tongue to reciting this prayer, certainly if one recites the text of the prayer ninety times (for in thirty days there are at most ninety prayers), we must say that one has accustomed himself to the correct version of prayer. Thus, if one then becomes unsure whether or not he has requested rain, he may assume that he has, for he has already accustomed his tongue to ask for rain.
This means that if one recites (according to the Sephardic custom) the words “Rofeh Choleh Amo Yisrael Barech Alenu” ninety times consecutively, one has accustomed himself that immediately upon concluding the blessing of “Rofeh Chloeh Amo Yisrael” to continue with the winter version of the “Blessing of the Years,” i.e. “Barech Alenu.” Similarly, according to the Ashkenazi custom, if one recites the words “Ve’et Kol Minei Tevu’ata Le’Tova Ve’Ten Tal U’Matar Livracha,” one has thereby accustomed himself to pray in the appropriate manner for the winter months.
The Bottom Line
The Rama (in his gloss on Shulchan Aruch, Chapter 114) rules in accordance with Maharam’s opinion and the Halacha indeed follows this view. Thus, one who repeats the above texts ninety times consecutively and later becomes uncertain whether or not he has requested rain in the Amida prayer can rest assured that he need not repeat the Amida, for he has already trained his tongue to pray correctly and his Halacha is equal to one who has prayed for thirty days while requesting rain in the Amida prayer.
Hagaon Harav Yaakov Nissan Rosenthal zt”l, head of the rabbinical court in Haifa and one of the generation’s luminaries, recounts how in his youth he merited living in the Sha’arei Chesed neighborhood of Jerusalem alongside Hagaon Harav Yaakov Moshe Charlap zt”l. On Simchat Torah, the great rabbis of the neighborhood and the surrounding vicinities would escort Hagaon Harav Charlap to the “Achva” synagogue amid much song and dance. They would sing a song the words of which were, “Ata Gibor Le’Olam Hashem etc. Mashiv Ha’Ruach U’Morid Ha’Geshem.” The young Rav Yaakov Rosenthal inquired as to why this song was sung, for there was no apparent connection between the song and the honor being bestowed upon Hagaon Harav Charlap! He was answered that they did not wish to waste precious time singing other songs. They chose to sing this song so that they could repeat these words ninety times in total in order to accustom themselves to request rain in accordance with the opinion of Maharam of Rottenberg which we have mentioned.