The Four Cups of Wine
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What Type of Wine
- It's preferable to use red wine for the four cups at the Seder. If there's white wine that's better than the red wine, Ashenazim say that one should have the white wine, while Sephardic practice is to have red wine anyway.  There is a dispute if it is permissible to mix red wine into white wine to color it.
- If one hates wine or if it gives him a headache (but not if it's going to make him sick in bed), nonetheless, he should try to have the wine to fulfill the mitzvah of the four cups of wine. 
- If there are no options and having wine or grape juice would make a person sick in bed he is exempt from drinking the four cups.
- Many authorities say that one may not use grape juice for the Seder, however, if one hates wine or will become ill, then there's is what to rely on to have grape juice. Others, however, permit having grape juice and adds that lechatchila women and children can use grape juice.
- If a person has no wine or grape juice can go to the store and buy grapes and press them and make kiddush on them.
- If someone has no wine they should recite kiddush upon the matzah, by reciting kiddush, al achilat matzah, then eat. Then he should eat karpas, start with maggid, continue with maror, and then korech.
- If someone doesn't have wine they should use chamar mdina, an expensive drink of that country. What does chamar medina include?
- Chamar Medina includes beer or cognac and does not include soda, lemonade, or water. Sephardim hold that coffee, tea, orange juice can not be used as chamar medina. Chamar medina is still relevant today.
- According to Ashkenazim, juice, coffee, or tea could be chamar medina, while milk or oil are not.
- One may not use soda because soda isn't considered Chamar Medina.
- Rav Heinemann holds that one may dilute wine with grape juice or water down to the point where the wine will be 4% alcohol.
- Regarding the bracha of hagefen, generally according to Ashkenazim it is possible to dilute wine down to 16% wine compared to water and according to Sephardim it must retain 51% wine to be hagefen. See Grape_Juice_and_Wine#Beracha.
Making Birchat HaGafen
- The Ashkenazi minhag is to make HaGafen on each cup of wine and a Bracha Achrona only on the last one. 
- The Sephardi minhag is to make HaGefen on the first and third cup of wine and a Bracha Achrona only on the last one. 
- There’s no Bracha Achrona on the first cup even if one knows that one will take longer than Shiur Ikul in explaining the Haggadah. 
Drinking at other times in the Seder
- One may drink wine in between the first, second, and third cups of wine but not between the third and fourth cups. 
- Even though one is permitted to drink between the first and second cup, one should be strict not to drink too much wine so as not to get drunk (and not be able to say the whole Haggadah). 
- According to Ashkenazim, in order to be permitted to drink between the first and second cup one must have had in mind to drink anything that comes later or that the wine was in front of them when he made the bracha (as long one didn’t have in mind not to cover that drink) because in this case no new bracha is needed on the wine between the first and second cup. 
- It’s totally permissible to drink beverages other than wine or intoxicating beverages between the first and second cup. 
- It’s permissible to drink between the second and third cup. 
- After drinking the four cups, it is prohibited to drink any other beverages, besides water.
If Four Cups are Drunk all at once
- If all four cups are drunk at once and not dispersed throughout the Seder in their proper place one doesn't fulfill his obligation. 
Amount to Drink
- See the Required Amount of Matzah and Wine for the Seder page.
- If someone spilled the cup before the bracha he should refill it so that it is full for the bracha. If he spilled after the bracha according to Ashkenazim he doesn't need to recite a new bracha since he can refill it with wine on the table that was in front of him and was in his mind. Some say that if the cup spilled one didn't fulfill the mitzvah and one needs to redo it. For example, if the cup spilled after the entire maggid he should refill it and repeat the maggid.
- Everyone at the seder should pick up the cup of Birkat Hamazon during birkat hamazon. Some say that it is sufficient if the one making the zimmun picks up his cup.
Obligation to Lean
- One must lean while drinking the four cups of wine. If for any of the cups one did not lean, according to Sephardim, one should drink the cup again. According to Ashkenazim, only for the second cup should one drink the cup again. 
- The practice is that one doesn't not pour his own cup. In order to demonstrate freedom, we have someone else pour each cup for us.
- A person should raise the third cup of wine for the birkat hamazon. If one is doing a zimmun it is sufficient for the one leading the zimmun to raise his cup. Otherwise everyone should raise their cup.
- Chazon Ovadia (pesach page 1). However, see Rav Shlomo Kluger in Sh"t Kinat Sofrim 95 who holds that the obligation of the four cups of wine is from the Torah.
- Shulchan Aruch O.C. 472:11. Mishna Brurah (472:38) explains that the idea of having red wine either reflects the verse “Do not look at wine when it is red” (Mishlei 23:31) or serves as a symbol to remember Pharaoh slaughtering the babies of Bnei Yisrael and bathing in their blood.
- Rama 472:11 writes that if the white wine is better one can have that instead of the red wine. Kitzur Shulchan Aruch 118:1 concurs. Kitzur Shulchan Aruch 118:1 adds that in countries where there is a fear of a blood libel, the minhag is not to use red wine. However, Chazon Ovadyah (Pesach vol 2 pg 11) writes that the Sephardic custom is to use red wine anyway. Rav Mordechai Eliyahu (cited by Mikrei Kodesh (4:15, n. 52) says that the "tirosh" grape juice in Israel that has a yellowish color is considered red wine in this regard.
- Mishna Brurah (320:56) cites a dispute whether it is permissible to mix red wine into white wine to color it or one should avoid this.
- Shulchan Aruch O.C. 472:10 says that even if one hates wine or it is harmful to his health one should push himself to have the wine to fulfill the mitzvah. Mishna Brurah 472:35 explains that one only has to have it if it gives one a headache but not if makes one sick in bed. Is the case where it is difficult for him to have wine an obligation to have it anyway or is it just the proper practice? Chazon Ovadia v.1 p. 53 discusses this and entertains the possibility that it is just a middah chasidut. However, the Orchot Chaim (Hilchot Leil Seder n. 5) holds that it is an obligation. Aruch Hashulchan 472:14 holds like the Orchot Chaim.
- Chazon Ovadia 1:4, Mishna Brurah 472:35, Aruch Hashulchan 472:14
- Mikrei Kodesh 2:35 (pg 130), Sh"t Chazon Ovadyah (in the note on pg 99-100), Halachos of Pesach (chapter 20, Sec B 5, pg 222) quoting Rav Moshe Feinstein rule that one doesn't fulfill חירות- having wine as a free man by having grape juice. However, Halachos of Pesach concludes that if one is unable to have wine one should have grape juice. Chazon Ovadia comes to this conclusion as well. Teshuvot Vihanhagot 2:243 writes that the Chazon Ish, Brisker Rav, and other Gedolim used grape juice at the end of their lives when they were unable to drink wine. Rav Shlomo Zalman Auerbach and the Chazon Ish held that one could use grape juice (Haggadah of Rav Shlomo Zalman Auerbach).
- Sh"t Mishneh Halachot 10:87, Nefesh HaRav (p. 185) in name of Rav Soloveitchik
- Gemara Bava Batra 97b, Shulchan Aruch O.C. 272:2
- Shulchan Aruch O.C. 483:1
- Rama 483:1, Mishna Brurah 483:1
- Shulchan Aruch O.C. 296:2 writes that one may make Havdalah on beer if it is Chamar Medina or other drinks besides for water. Birkei Yosef 296:3 clarifies that the Shulchan Aruch's language of "or other drinks" didn't mean to include milk and oil, but rather he meant other types of Chamar Medina and exclude water even if the people of the town only drink water. Sh"t Igrot Moshe 2:75 rules that soda is just like water, isn't Chamar Medina, and thus, can not be used for Havdalah. Sh"t Vayan Avraham (Izrael) Siman 34 (pg 63) writes that he remembers in the holocaust the question arose whether lemonade could be used for Havdalah and he concludes that it just like water and can’t be used for Havdalah. Yalkut Yosef 296:8 writes that one may not use coffee, tea, orange juice, or soda for Havdalah, but one if there's no wine in the city, one may use beer or cognac which are considered Chamar Medina; Chazon Ovadia, Hilchot Shabbat, Chelek 2, Page 408 specifies that coffee, tea, milk, and fruit juice are not considered chamar medina, and therefore one may not make havdalah with them. More sources can be found in Yabia Omer OC 3:19 for this approach.
- Rav Chaim Kanievsky in Kovetz Teshuvot 1:57 asked Rav Elyashiv whether a sick person could recite havdalah on tisha b'av on wine or chamar medina. Rav Elyashiv responded that they should use beer or another drink. Rav Chaim responded that the Chazon Ish thought that nowadays nothing including beer is chamar medina since wine is so common and even orange juice he was hesitant to allow using it as chamar medina.
- As for the definition of chamar medina Mishnah Brurah 272:24 says that even beer is only permitted in a place where it is a common drink. Mishna Brurah 272:25 prohibits the use of milk or oil, and Mishna Brurah 272:30 permits the use of liquor. Rav Avigdor Neventzahl in Biyitzchak Yikare footnote 25 says that according to Rav Shlomo Zalman Auerbach milk is not allowed even in places where it is commonly used like Switzerland. He also says that juice, tea, or coffee maybe permitted but soda is definitely not because it is just like water. Rav Moshe Feinstein in Iggerot Moshe OC 2:75 defines chamar medina as something you would serve to guests who you want to show respect to. Tzitz Eliezer 8:16 and 14:42 allows using coffee, tea, or milk as chamar medina when there is no wine available. Igrot Moshe 2:75 says that in an extenuating circumstance tea or milk could be used as chamar medina.
- Sh"t Igrot Moshe 2:75 rules that soda is just like water and can not be used for Kiddish. Rav Avigdor Neventzahl in Biyitzchak Yikare 272 fnt. 25 agrees.
- Rama 474:1
- S”A 474:1
- Halichot Shlomo 9:24
- The Mishna (Pesachim 117b) states that it is permitted to drink wine between the 4 cups of wine, except between the third and fourth cups. The Rashbam (108a s.v. Bein Shelishi) explains that one may drink wine between the first, second, and third cups because it serves as an appetizer for the Matzah. However, after Birkat HaMazon, when there’s no more need to eat Matzah, drinking an extra cup appears as though one is adding on to the established 4 cups of wine. See Reshimot Shiurim (Sukkah p. 139) for an explanation of why it only appears as adding but does not violate Bal Tosif.
- The Yerushalmi (Pesachim 10:6), however, explains that one should not drink between the third and fourth cups so as not to get drunk, which would prevent a person from saying Hallel. Drinking between the earlier cups is not an issue because during a meal, wine is not as intoxicating.
- Rambam (Chametz U'Matza 7:10), Tur, and S”A 473:3 and 479:1 codify the Mishna. Mishna Brurah 479:5 writes that based on the Yerushalmi, one also may not drink any intoxicating drink, and as a stringency according to the Rashbam, one may not drink Chamar Medina (which is valid for the 4 cups).
- Shulchan Aruch 473:3 writes that even though it’s permitted to drink but one should be careful not to drink too much wine so as not to become intoxicated and become unable to finish the Haggaddah. Darkei Moshe and Mishna Brurah 473:14 write that such is our minhag. The Baal Hameor (Pesachim 24a) contends that drinking between the first and second cup is permitted, while the Ramban (ad. loc) and Ran argue that once the second cup is poured it is forbidden to drink another cup.
- Mishna Brurah 473:13 writes that according to Ashkenazim that make a bracha on each cup of wine and making a bracha on wine unnecessarily is forbidden because it looks like one is adding to the established number of cups of the night. Therefore, if the wine was on the table as one made the bracha or one had intention to cover anything that comes later, it’s permitted to drink the cups.
- Mishna Brurah 473:16
- Mishna Brurah 473:12
- Kitzur Shulchan Aruch 119:9
- Shulchan Aruch 472:8
- Kovetz Teshuvot Vpesakim Chodesh Nissan p. 72
- Nefesh Harav p. 186 quoting Rav Moshe Soloveitchik as holding that the four cups were established as a way of having the haggadah recited over a cup of wine and if the wine spilled one doesn't fulfill that obligation.
- Chazon Ovadia v. 2 p. 182, Nitai Gavriel 99:9. Chazon Ovadia explains that since it is a mitzvah for everyone to drink it is considered birkat hamazon over a cup of wine for everyone.
- Chazon Ovadia citing Shiurei Tahara 80:16
- Shulchan Aruch O.C. 472:7, Yalkut Yosef 472:13
- Rama 472:7 writes that if one forgets to lean, he must only repeat for the first two cups. Mishna Brurah (472:21) notes that in general one should not repeat the first cup because doing so will require one to make another berakhah. Preferably, one should have in mind that one may drink in between the first and second cup and then if one drinks the first cup without leaning, one would be able to drink it again without a berakhah.
- Rabbi Eli Mansour pg. 4
- Guide to Practical Halacha (v. 5 p. 171 n. 14)