Siman 474

Our teacher, the Beit Yosef, wrote: One drinks the second cup, and does not recite over it either an initial blessing or a final blessing, for one does not recite "borei peri ha-gafen" except over the cup of kiddush and over the cup of birkat ha-mazon. And one does not recite "al ha-gafen" except after the fourth cup. Thus far his words, for he holds that the Haggadah and the Hallel do not constitute an interruption. Therefore, the blessing of kiddush exempts the second cup from a blessing, and the blessing over the third cup, which is the cup of birkat ha-mazon—exempts the blessing of the fourth cup. And why does one not recite a final blessing over the second cup? Because it is wine before the meal, which exempts the wine within the meal, and birkat ha-mazon exempts it from a final blessing as during the rest of the year, as I have written in siman 174 (see the Ba'al HaMaor and Milchamot).

But our teacher, the Rema, wrote: And the custom among the Ashkenazim is to recite the first blessing over each and every cup. But regarding the final blessing – one only recites it after the final one alone. And such is the opinion of most of the Geonim. Thus far his words, and he holds that the Haggadah and the Hallel constitute an interruption. And even though if so, why should one not recite a final blessing over the first and over the third, since they have no connection to one another? Rather, perforce one must say that it does not constitute an interruption; if so, why is a first blessing required for the second and for the fourth? And they answered that since the sages ordained these four cups to be drunk in the manner of freedom, and each and every one is a mitzvah unto itself; therefore, they do not combine with one another to be exempted with one blessing, but rather one must bless over each one individually (Magen Avraham). And this is not sufficient. And there are those who added to say that it is as if he stipulated over each and every cup that it should only exempt itself (Taz). And this is more puzzling, for from where do we have this stipulation?

And in my humble opinion it appears: Behold, it is written in the Maharil that one must recite a blessing over each and every cup, even though the Rosh ruled not to recite a blessing. The Tosafot ruled that one should recite a blessing, and it is forbidden to derive benefit without a blessing, and a doubt regarding a prohibition is resolved stringently. Thus far his words. And this is not understood at all: For on the contrary, a doubt regarding blessings is resolved leniently (and the Chok Yaakov already raised this difficulty against him and remained in wonderment, see there). Therefore, it appears to me that this is the explanation: Behold, it is certain that there is a doubt whether the Haggadah constitutes an interruption or not, and therefore we ruled in the previous siman regarding karpas that one should not eat a kezayit. And if he did eat—he should not recite an after-blessing, for a doubt regarding blessings is resolved leniently, as I wrote there. If so, it is obvious that he should not recite an after-blessing. But if so, why should he drink? Out of doubt he should not drink and not recite a blessing, and why should he enter into a doubt of deriving benefit without a blessing? Rather, what must you say? That he is compelled to drink because of the commandment of the sages who instituted four cups. If so, how can we say to a person: drink a prohibition out of doubt? For he could say: it is not pleasing to me to enter into a doubtful prohibition, to derive benefit without a blessing! Rather, we say to him: drink and recite a blessing, and it turns out that we permit him to recite a blessing. And automatically, according to the institution of the sages—it is necessary that the intention was not to exempt the second cup from a prior blessing. But regarding the after-blessing, since there is a doubt—a doubt regarding blessings is resolved leniently.