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With regard to written texts, a Torah is invalidated if the same character is written for what should be distinct letters (e.g. כ and ב). However, with regard to the spoken language and people who are unable to pronounce a letter correctly, the Midrash (Shir HaShirim Rabba parsha 2, on Shir HaShirim 2:4 [hattip @DoubleAA]) interprets the verse "ודגלו עלי אהבה" to say that G-d counts their intent, not their spoken words (the case used in the derash is the extreme example where one read "ואהבת" ["and thou shall love"] as "ואיבת" ["and thou shall hate"]).

If, however, someone is able to pronounce the sounds correctly but was taught by their teachers the wrong pronunciation, and never bothered updating his pronunciation even after finding out the error, is his mispronunciation halachically valid (e.g. for kriyat shema, parshat amalek, tefilla, etc.)?

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    See Bava Basra 21a-b, for a story involving mispronouncing parshas 'Amalek. – Fred May 14 '15 at 22:49
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    related judaism.stackexchange.com/q/18529/759 and all the questions linked therein – Double AA May 14 '15 at 23:04
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    Are you specifically asking concerning mispronouncing that alters the meaning of the word? Otherwise, your scenario reflects similarity to regional accents. For example, theword "Torah" is technically pronounced TOE-RAH or TOE-RA but some communities say TA--RA and TOY-RAW. In addition, Ashkenazim and Sephardim place word stress differently; either on the medial or final sound. en.m.wikipedia.org/wiki/Modern_Hebrew_phonology – JJLL Nov 18 '15 at 1:13
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    @Dude The people who base their pronunciation on mountains of historical and linguistic evidence. In any event, the question doesn't specify which would be considered the only correct one, so is unbiased to any side, and is asking theoretically. There could always be application in unusual Baal Teshuva cases or post-medical treatments or something. – Double AA Nov 19 '15 at 7:00
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