This Sunday and Monday will be Rosh Chodesh Adar-Bet.
When the 3rd Shabbat meal continues into the night, one still inserts רְצֵה during Birkat Hamazon.
When one starts a meal on Erev Rosh Chodesh and eats a Kezayit (the size of an olive) of bread after dark, one inserts יַעֲלֶה וְיָבוֹא during Birkas Hamazon.
What happens when both of the above happen together?
Some Poskim say that if Rosh Chodesh is on Sunday and one eats a Kezayit of bread after dark during the 3rd Shabbat meal, then one inserts both רְצֵה and יַעֲלֶה וְיָבוֹא during Birkas Hamazon.
However, other Poskim argue that mentioning both is a contradiction – since Shabbat and Rosh Chodesh aren't on the same day.
Therefore it's best to be careful not to eat bread after dark at the 3rd Shabbat meal when Rosh Chodesh is on Sunday - and then only רְצֵה is added.
Source: Kitzur Shulchan Aruch 44:17
וְאִם אָכַל שֶׁהַתְחָלַת הַסְּעוּדָּה הָיְתָה בַּיּוֹם, צָרִיךְ לְהַזְכִּיר מֵעִנְיַן הַיּוֹם, אַף עַל פִּי שֶׁמְבָרֵךְ בַּלַּיְלָה.
וְאִם אָכַל בְּעֶרֶב רֹאשׁ חֹדֶשׁ וְנִמְשְׁכָה סְעוּדָּתוֹ גַּם תּוֹךְ הַלַּיְלָה, וְאָכַל גַּם בַּלַּיְלָה כַּזַּיִת פַּת, וּלְמָחָר הוּא רֹאשׁ חֹדֶשׁ, אוֹמֵר רְצֵה וְגַם יַעֲלֶה וְיָבֹא. וְכֵן בַּחֲנֻכָּה וּפּוּרִים.
וְיֵשׁ חוֹלְקִין, מִשׁוּם דַּהֲוֵי כְּתַרְתֵּי דְּסָתְרֵי. עַל כֵּן יֵשׁ לִמְנוֹעַ שֶׁלֹּא לֶאֱכוּל אָז בַּלָיְלָה.
- Danny Schoemann
Thursday, 27 Adar-1 5784
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