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In 3 Enoch, Ishmael learns that Israel has broken the law from its first letter to its last. Rabbinic tradition in Lamentations Rabbah has the letters accuse Israel, making the entire alphabet evidence of disobedience.
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2500 BCE
1000+ CE

3 Enoch 44:9

Hebrew Book of Enoch
Pseudepigrapha, Apocalypses
Then the Holy One, blessed be He, answered every one of them, saying: "Since these wicked do sin so and so, and transgress with such and such transgressions against me, how could I deliver my great Right Hand in the downfall by their hands (caused by them)". In that moment Metatron called me and spoke to me: "My servant! Take the books, and read their evil doings!" At once I took the books and read their doings and there were to be found 36 transgressions (written down) with regard to each wicked one and besides, that they have transgressed all the letters in the Tora, as it is written (Dan. ix. 11): "Yes, all Israel have transgressed your Law". It is not written 'al torateka but 'et torateka, for they have transgressed from 'Aleph to Taw, 40 statutes have they transgressed for each letter.
Date: 400-600 C.E. (based on scholarly estimates)

Lamentations Rabbah Petichta:24

Aggadah
Rabbinic
The Holy One blessed be He said to Abraham: ‘Let the twenty-two letters come and testify against Israel.’ Immediately, the twenty-two letters came. Alef came to testify against Israel that they violated the Torah. Abraham said to it: ‘Alef, you are the leader of all the letters, and you come to testify against Israel on their day of distress? Remember the day that the Holy One blessed be He revealed Himself on Mount Sinai and began with you, “I am [anokhi] the Lord your God” (Exodus 20:2) – no nation other than my descendants accepted you, and you come to testify against my descendants?’ Immediately, alef stood to one side and did not testify against them.
Date: 500 C.E. (based on scholarly estimates)
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Notes and References

#7616
“... v. "Moreover, it was recorded that they . . . all the letters of the Torah": a paraphrase of obscure Heb. following the E text. The other MSS appear to be corrupt. w. " 'Alep to Taw": the first and last letters of the Heb. alphabet. Cf. LamR proem 24, where the twenty-two letters of the alphabet come to testify against Israel's transgressions of the Law. ...”

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