עובר לעשייתן means that you have to say the bracha before you do the mitzvah.
Do you have to finish the Bracha before you finish the Mitzvah, or is it enough that you began the bracha before you finished the mitzvah.
(There is a similar question regarding זמני תפילה. Is it enough to begin during the zman even if you finish after the zman, or do you have to complete the tefilla during the zman. This is a machlokes between the Mishna Berura and the Aruch HaShulchan. Mishna Berura, you must complete. רל'ג ס"ק י'ד and קכ'ד ס"ק ז. Aruch HaShulchan, it's enough to begin during the zman (his raya being from Tosfos in Brachos 7a about Bilaam.) ק'י סע' ה and קכ'ד סע' ו. I do not think this has any logical connection with our discussion, just like our discussion has no connection with Birkas Hanehenin.)
Reb Moshe says that as long as you began the bracha before the mitzvah was finished, it doesn't matter if the mitzvah was completed before you finished the bracha. What matters is that you begin the bracha עובר לעשייתו. So (point #1) you can begin the Bracha while the mitzva is taking place, and then (point #2) you can finish the bracha after the mitzva has already been completed.
The Chayei Adam vehemently says the contrary.
Reb Moshe's shittah is based on a Rosh in Halachos, but the Rosh in the Teshuvos seems to say like the Chayei Adam. I do not think Reb Moshe saw the Teshuvos inside. Whether he would change his mind if he did? I doubt it. I know enough of Reb Moshe to be confident that he would say that the Rosh in the Tshuvos isin the name of Rabbeinu Tam, and the Rosh in Maseches Shabbos is saying his own opinion, and Reb Moshe is paskening like the Rosh.
I do need to point out, though, that the Aruch Hashulchan agrees with Reb Moshe on one point and argues with him on the other. The Aruch Hashulchan brings the Chayei Adam's requirement that the bracha begin before the mitzva begins, and he disagrees with this point. He agrees with Point #1 in Reb Moshe, that you do not have to begin the bracha before you begin the mitzvah, but then he says that you do have to finish the bracha before you finish the mitzvah, or finish them at the same time. This is contrary to Reb Moshe's Point #2, which is that as long as you began the bracha עובר לעשייתן, it is fine if you finish the mitzva before you finish the bracha.
The question arises regarding the nature and the halacha of the father's bracha of להכניסו, which seems to conflict with the rule of עובר in that it is said after the removal of the ערלה. To explain why this is done, Rabbeinu Tam says that this bracha is not on this particular act of mitzvas milah, it is a praise to Hashem that He gave us this mitzvah, it is a ברכת שבח והודאה, and, as such, it does not need to conform to the rule of עובר לעשייתו. The Rosh, on the other hand, holds that it is a regular ברכת המצוה, and, as such, needs to be עובר לעשייתו. So the Rosh in Shabbos 137b says that the minhag is to say this bracha immediately after the Mohel's bracha, and although it may be after the removal of the orla, it is before the pri'ah. Because Pri'ah is essential to the fulfillment of the mitzvah, a bracha said prior to the pri'ah is עובר לעשייתו.
Reb Moshe (YD 155, end,) says that this can not mean that the mohel should wait to begin the pri'ah for the father to make the bracha. To do so would be cruel. It means that the father begins the bracha before the completion of the mitzvah. Clearly, Reb Moshe holds that what matters if that you begin the bracha prior to the completion of the mitzvah.
The Chochmas Adam (149:19) says, absolutely not. He says that עובר means that you finish the bracha before you begin the milah, and certainly that you finish the bracha before you finish the milah. He severely disparages those mohalim who finish the mitzva before finishing the bracha.
Here are the relevant sections.
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