Q. There are many references in tefila and in viduy to sins and transgressions that we have committed and we should be punished or even put to death for them. Since a person has to be very cautious with his words, why is there no issue of “al iftach adam pe lasatan” when saying them? Wasn’t Moshe Rabbenu punished for saying he should be erased from the Torah?

A. In Talmud (Brochos 19a) Abaye teaches that one should not pray saying; “Master of the Universe, I have sinned greatly before you, and you have not exacted from me one thousand of the punishment I deserve,” since one should never give Satan an opening to demand he should be indeed be punished (Maharsho Kesubos 8b). Rav Yosef quotes a supporting posuk (Yishayahu 1: 9); “Has Hashem not left us a remnant, we would have almost been like Sodom” and in the next verse, the prophet says in rejoinder; “Hear the word of Hashem, chiefs of Sodom.”
Horav Shlomo Miller’s Shlit’a opinion is that it depends how one recites. If it is an expression of viduy and confession of one’s sins to show repentance and avoid repeating in the future, it is proper and correct. Also if one davens that he should not recur in the mentioned transgressions done, it is appropriate and desirable. However, one should indeed be careful in the wording of his tefilos.

Rabbi A. Bartfeld as revised by Horav Shlomo Miller Shlit’a