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Normally, if me and my good friend Shimon complete (finish) a Bracha at the same time, I may not say Amen after his bracha.

However, if I recall correctly, an exception to this is made by the bracha of Haskivenu said by Maariv (the 2nd bracha after Shema). There I should say Amen to the Chazzan's recitation of "Shomer Amoi Yisrael La'ad" regardless of whether I also completed it at the same time.

Why is this so? What is so special about this Bracha that it deviates from the norm?

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It's not unique. It's because it's the last blessing in a series. The same is true for bone (b'rachamav) Y'rushalayim after a meal and the final b'racha of Halel and p'suke d'zimra.

Specifically, SA OC 215:1 has that we say amen to our own b'racha in each of these cases even without hearing someone else simultaneously, and I believe S'faradim follow this rule. Rama there limits that rule to bone Y'rushalayim.

Now, Rama there does not discuss the case of finishing the other b'rachosHashkivenu et al. — simultaneously with another's b'racha.

However, Aruch Hashulchan :4 notes that the Rama's limiting to bone Y'rushalayim is because that that's the only b'racha on which one must answer amen to his own (so as to differentiate the d'oraysa three b'rachos from the fourth): we don't answer amen to our own Hashkivenu et al. (where it's permitted but not required to do so) so as to lend more oomph to the differentiation afforded by answering bone.

This AHS supplies us, perhaps, with the reason answering one's own bone Y'rushalayim (and the others) is appropriate when hearing another's b'racha simultaneously. Since there's really nothing wrong with doing so (as there usually is when finishing a b'racha oneself), it's appropriate when one's heard someone else's b'racha.

As to why the last blessing in a series has the you-may-answer-your-own rule, I don't know.

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We say Amen after bone (b'rachamav) Y'rushalayim to differentiate between the first 3 blessings which are biblical and the 4 blessing which is rabinical: Shulchan Aruch HaRav 188:1 (see footnotes for sources - hebrewbooks.org/pdfpager.aspx?req=25072&pgnum=556) –  Menachem Nov 17 '11 at 16:16
    
@Menachem, that's why Ashk'nazim do it, yes. But that's not why we say "amen" to it when finishing at the same time as another, which is what the question asked: for that halacha, it's no different from Hashkivenu and the end of Halel and p'suke d'zimra. –  msh210 Nov 17 '11 at 17:29
    
Boneh Yerushalayim has a specific requirement that the Hazan himself says Amen at the end of the Berachah, to split the different types of Berachoth, as @Menachem said. –  Seth J Nov 18 '11 at 17:31
    
@SethJ, yes, but without that special halacha the b'racha would still have the rule, as Hashkivenu et al. do, that you answer another's who finishes with you. –  msh210 Nov 18 '11 at 17:43
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A) it's verachamav with no dagesh in the bet. B) Another example of brachot that end a series is ga'al yisrael by shacharit. that is why some don't think the custom of ending the bracha with the chazzan solves the amen issue. –  Double AA Nov 23 '11 at 19:51
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