When on the night of the 15th must the Matzah be eaten?

Not before nightfall/Tzeis Hakochavim:[1] One does not fulfill the Mitzvah of eating Matzah prior to nightfall [i.e. Tzeis Hakochavim].[2] [Thus, if he ate Matzah prior to nightfall, even during Bein Hashamshos, he must repeat and eat a Kezayis of Matzah at night. Nevertheless, if he ate the Matzah during Bein Hashamshos, it is questionable whether a blessing is to be recited.[3] Thus, in such a case one should be Yotzei with the blessing of another person.[4]]

Before midnight:[5] One is required to fulfill the Mitzvah of eating Matzah prior to midnight.[6] [If one eats the Matzah only after midnight, some Poskim[7] rule he does not fulfill his obligation and has thus lost the Mitzvah. Other Poskim[8]rule he can nevertheless fulfill the Biblical Mitzvah up until Alos Hashachar. Other Poskim[9] rule that this matter is left in question, and hence one is to be stringent like both opinions, and eat Matzah without a blessing. Practically, if one did not yet eat the Matzah and it is already after midnight, he is to eat the Matzah without the blessing of “Al Achilas Matzah.”[10] If it is already close to midnight and one did not yet eat the Matzah, he is to skip from wherever he is holding and perform Motzi Matzah before midnight. The same applies to a person who awoke from a sleep moments before midnight that he should say Kadesh and immediately afterwards recite Motzi Matzah.[11] This applies for both the first and second Seder.[12]]

Tashlumin:[13] If one did not eat Matzah on the night of the 15th due to reasons beyond his control, he is unable to makeup the Mitzvah on another night or day of Pesach. Accordingly, when one eats Matzah on the other nights and days of Pesach he does not recite the blessing of “Al Achilas Matzah” even though he has yet to eat Matzah from the start of Pesach, and hence has never yet said a blessing over it.

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[1] Admur 472:2; Levush 472:1; Terumas Hadeshen 137; Tosafus Pesachim 99b in name of Mahariy Krubil; Rosh 10:2; Shulchan Gavoa 472:3; P”M 472 M”Z 1; Kaf Hachaim 472:7

[2] The reason: The eating of Matzah is connected [Hekesh] to the eating of the Pesach lamb, as the verse [Bamidbar 9:11] states “Al Matzos Umerorim Yochluhu,” and by the Pesach lamb it states [Shemos 12:8] “Veachlu Es Habasar Balayla Hazeh” from which we learn it must be eaten by actual night. Now, since the eating of the Pesach lamb can only be fulfilled at night so too the eating of Matzah.  [Admur 472:2; Levush 472:1; Terumas Hadeshen 137; Tosafus Pesachim 99b in name of Mahariy Krubil; Rosh 10:2]

[3] P”M 472 M”Z 1

[4] Kaf Hachaim 472:7

[5] Admur 458:2 “One is required to eat the Matzah prior to midnight, just like the law regarding the Karban Pesach which may only be eaten until midnight,”; Admur 639:20 “And one is to beware to eat in the Sukkah prior to midnight, just as is required regarding eating Matzah”; 477:6 regarding Afikoman; See 472:2 regarding the Hekesh being used to obligate eating Matzah after Tzeis Hakochavim [Vetzaruch Iyun why the end time was not mentioned in this Hekesh, and why we make the Hekesh for the end time only regarding Matzah and not the four cups, also Tzaruch Iyun why in 475:20-23 no mention of Chatzos was made; See here: http:::shulchanharav.com:text.asp?index=128712&arc_id=138425]; Michaber 477:1 and Beis Yosef 477 regarding Afikoman;  Degul Merivava 477; Shaareiy Teshuvah 477:1; M”B 477:6 “One must be very careful”; Biur Halacha 477; Kaf Hachaim 475:64; 477; Piskeiy Teshuvos 477:4

[6] The reason: As just like the Karban Pesach may only be eaten until midnight, so too the Matzah may only be eaten until midnight, as the verse states Al Matzos Umerorim Yochluhu, thus teaching us that the eating of Matzah is connected, and follows similar laws, to the Pesach [Admur 458:2] This follows the opinion of Rebbe Elazar Ben Azaria, brought next.

[7] Reb Elazar Ben Azaria in Pesachim 120b; Zevachim 57b; Tosafus Zevachim ibid; Megillah 21a; Piskeiy Tosafus Pesachim 334; Zevachim 33; Rabbeinu Chananel in Arvei Pesachim; Semag in name of Riy; Mordechai end of Pesachim; Rabbeinu Yerucham 5:4; Conclusion of Or Zarua; Hapardes 9:16-26 “It is forbidden to eat Matzah after midnight”; Kol Bo 90 in name of Riy; See Biur Halacha 477:1 “Viyihei Zahir”

[8] Rebbe Akiva in Pesachim and Zevachim ibid; Rambam Karban Pesach 8:15; Chametz Umatzah 6; Rif [brought in Mishkanos Yaakov 139] Rav Hamaggid; Baal Haitur; Or Zarua in name of Rav Yaakov of Krubil; Kol Bo 90 in name of Rav Shmuel Shakli; See Biur Halacha 477:1 “Viyihei Zahir”

[9] Rosh; Rashba; Ran end of Megillah chapter 2; Rokeiach

[10] Degul Merivava 477; Shaareiy Teshuvah 477:1; P”M 477 M”Z 1; Derech Hachaim; Tov Ayin 38:87; Ikarei Hadat 19:14; Misgeres Hashulchan 119:11; Aruch Hashulchan 477:5; M”B 477:6; Biur Halacha ibid; Kaf Hachaim 473:16; 475:64; Beis Halevi 1:34; Nitei Gavriel 91:1; Piskeiy Teshuvos ibid

Other opinions: Some Poskim rule that the final ruling of the Talmud is like Rebbe Akiva that the Mitzvah of Matzah applies throughout the night, until Alos Hashachar. [Mishkanos Yaakov 139; Or Yisrael 475; Or Sameiach 6:1; Sdei Chemed Mareches Chametz Umatzah 14:11; See Nitei Gavriel ibid footnote 1] According to all, the blessing may no longer be said once Also Hashachar has arrived. [Hisorerus Teshuvah 269; Piskeiy Teshuvos ibid]

[11] Degul Merivava 477; Shaareiy Teshuvah ibid; M”B 477:6; Ashel Avraham Butchach 477; Kaf Hachaim 477:10

[12] Admur 481:1 “There is no difference between the first and second night in any other matter”; Nitei Gavriel 91:5

Other opinions: Some Poskim defend the practice of those who recite a blessing over the Matzah even after midday. [Darkei Chaim Veshalom 605; See Nitei Gavriel ibid footnote 6]

[13] Admur 476:33; Chok Yaakov 475:24; Elya Raba 475:13; Tosafus Sukkah 27a; Kol Bo 50; Birkeiy Yosef 482:2 in name of Tzeror Hachaim and Shiyurei Bracha in name of Hapardes; Shaareiy Teshuvah 482; Kaf Hachaim 475:75; 482:11