based on:

SHABBAT Law #s11: "Is it necessary to pour wine into the cup of Kiddush and Havdalah until it spills over? Is that not a waste?"

There is a custom to fill the havdalah cup until it is overflows, as that is considered a portent for overflowing blessings. Neither the issue of being wasteful nor that of treating food disrespectfully applies in this situation, because it is only a small amount that is being spilled out, especially today when virtually everyone has a plate underneath the cup so anyway the spilled wine need not be wasted.

Some authorities suggest that this should also be done with any cup of wine designated for blessing over a mitzvah. Indeed, the [Lubavitcer] Rebbe as well as some Sefardic rabbinical authorities suggested it should be done every single time we make kiddush. In this way, the overflowing of the wine symbolizing an overflowing of blessings will occur not only in the beginning of the week on Saturday night, but every time we make kiddush and do other mitzvos which require a cup of wine, such as at a bris milah circumcision, under the chuppah at a wedding and at the meals with a minyan in the week following [and the blessings after eating a meal with bread if a cup of wine is poured].

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Please note that these laws apply in general situations. In unique circumstances, a different law may apply.

If you are unsure whether what you read here applies to your particular situation, please consult a rabbinic authority.

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