F. ✍️ Began a meal on Erev Rosh Chodesh and is reciting Birchas Hamazon on Rosh Chodesh: [1]
If one began eating a meal during the day of Erev Rosh Chodesh [before sunset] and concluded the meal at night after Rosh Chodesh has begun, then if he ate a Kezayis of bread after nightfall he is to recite Ya’aleh Veyavo in Birchas Hamazon. If he did not eat a Kezayis of bread after nightfall, he is not to recite Ya’aleh Veyavo in Birchas Hamazon.
Rosh Chodesh that falls on Motzei Shabbos:[2] If one began eating a meal on Shabbos Erev Rosh Chodesh, such as Shalosh Seudos, and the meal ended after nightfall after Rosh Chodesh already begun, then if he did not eat a Kezayis of bread after nightfall he is to say only Ritzei and not Ya’aleh Veyavo in Bentching. If, however, he ate a Kezayis of bread past nightfall then he is to recite both Ritzei and Ya’aleh Veyavo.[3]
Davened Maariv or said Havdala on Motzei Shabbos Rosh Chodesh:[4] If one recited Havdala or Davened Maariv on Motzei Shabbos prior to Bentching, then Ritzei is not to be said, and hence if one ate a Kezayis after nightfall he is to only recite Ya’aleh Veyavo.[5] If one said Baruch Hamavdil prior to Bentching, it receives the same law as one who Davened Maariv and hence Ritzei may not be recited.[6]
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Q&A If one Davened Maariv after Plag Hamincha on Erev Rosh Chodesh and then ate a meal, is Ya’aleh Veyavo to be recited?[7] Yes.
If one ate bread during Bein Hashmashos of Erev Rosh Chodesh-Rosh Chodesh, is he to say Ya’aleh Veyavo? If he ate a Kezayis of bread after nightfall, then Ya’aleh Veyavo is to be recited. If, however, the Kezayis was only eaten during Bein Hashmashos, then it is questionable as to whether Ya’aleh Veyavo is to be recited.[8]
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[1] 188:17; Ketzos Hashulchan 47:9
Background:
Admur ibid records a dispute in this matter. Some opinions rule, as stated above, that one only recites Ya’aleh Veyavo if he ate a Kezayis of bread after nightfall. Others rule that even if he did not eat a Kezayis after nightfall he is to recite Ya’aleh Veyavo. Practically, the custom is like the former opinion.
[2] 188:17; Ketzos Hashulchan 47:10 footnote 22; See M”B 188:33
[3] Admur ibid; Taz 188:7, brought in M”B 188:33 as 2nd opinion
Background:
Admur ibid records a dispute regarding whether one may say both the previous days and current day’s extra prayer within Bentching, if he began a meal during the day and it continued into the night, with him eating a Kezayis of bread at night. [M”A 188:18 prohibits; Taz 188:7 permits if said in order] He concludes like the Taz ibid that one may do so if the order in the Benching is that he first recites the previous day’s event and then recites the current night’s event. [Such as one who had a meal on Shabbos afternoon and Motzei Shabbos is Rosh Chodesh and Ritzei precedes Ya’aleh Veyavo.] If, however, the night’s event precedes the previous day’s event then one may not say both prayers even according to the lenient opinion, as it is a contradiction. One is thus to only say the current nights event. [Admur ibid; Ketzos Hashulchan ibid; Taz 188:7; brought in M”B ibid]
Other opinions: Some Poskim rule one never recites the additions of two days, as it appears contradictory, and hence on Motzei Shabbos Rosh Chodesh one only recites Ya’aleh Veyavo if a Kezayis was eaten at night. [M”A 188:18 and 419:1; 2nd opinion in Admur ibid; first opinion in M”B ibid] Others rule one is to only recite Ritzei and not Ya’aleh Veyavo. [Darkei Chaim Veshalom 307; See Shoel Umeishiv 3:1-373]
[4] Admur ibid; Ketzos Hashulchan 47:8
[5] The reason: As it is a contradiction to have prayed the prayer of the next day and then mention the previous day. [ibid]
[6] Admur ibid leaves this matter in question and concludes that Shev Veal Taaseh Adif, that it is better not to say it. Vetzaruch Iyun as to the intent of the parentheses there; Ketzos Hashulchan 47:8
[7] Magen Avraham 419:1
[8] The wording in Admur is “He ate a Kezayis of bread after it becomes night”; See Piskeiy Teshuvos 188:19 in name of Ashel Avraham of Butchach; This matter is a Sfek Sfeka as perhaps we rule like the opinion that says one follows the time of the Bentching, and even if not, perhaps Bein Hashmashos is night. Vetzaruch Iyun!