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There are several customs that relate to Yahrtzeit, such as lighting a candle, saying Keil Malei Rachamim, etc. These typically are done on the Yahrtzeit, though some do it on the preceding Shabbos.

Which day is counted for a person who died Bein HaShemashos? Do we go after the preceding day, or the following day? That is, if they died during the Bein HaShemashos between the fifth and the sixth, is the Yahrtzeit observed on the fifth or the sixth?

Even for customs not observed on the Yahrtzeit itself, there are practical applications. If the fifth is a Wednesday and the sixth is a Thursday, is Keil Malei Rachamim said on Monday or Thursday leining? If the fifth is a Friday and the sixth is a Shabbos, for those who light on the previous Erev Shabbos, in which week is it lit?

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    Since this is only a custom, you probably only need to "worry" about maybe ~15 minutes of doubt after sunset, not all the way till when we'd finish Shabbat. – Double AA May 22 '17 at 18:16
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    This should be an issue for anything that occurs Bein Hashmashos ie a boy born - what day is the 8th day for the bris etc. – Earl May 22 '17 at 19:45
  • @Earl I​​​​​​​​​​​​​​​t is indeed. eg judaism.stackexchange.com/q/85768/759 – Double AA May 22 '17 at 20:26
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Nitei Gavriel Aveilus 2 - 77:1 says that there are those that say it is best to hold the Yahrzheit the earlier day, those that say it is best to hold the Yahrzheit the later day, and those that say to hold the Yahrzheit both days.

Those that say the Yahrzheit should be held the earlier day include Zechor L'Avraham, Shut Knaf Ranana OC 55, Darchei Hachaim 34:8, Gesher Hachaim 32:12 - who seems to say that both days should be held if there are no other Availim. A reason he mentions in the footnotes is that all that is done on the Yahrzheit is a Tikun for the Neshama, therefore it should be done earlier this way the Neshama will for sure have the Tikun on time.

Those that say the Yahrzheit should be held the later day include Duda'ai Sadeh 98 and the Munkatcher Rabbi in Sefer Gan David. A reason he mentions is that whenever there is a doubt we delay (Pironiyos). And since the day of the Yahrzheit is a day of bad Mazal for the descendents therefore it is delayed to the later day.

Those that say both days should be held includes Darchei Hachaim 34:8 - who mentions there are those that do both days, however he concludes that it should be done the earlier day, Duda'ai Sadeh 98, Gan David, Shut Shaarei Tzedek YD 198.

  • Curious. Do any of these commentaries apply similar rules to the last day of Kaddish for a parent? – DanF May 22 '17 at 20:15
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From This OU article

Q: When is the yahrzeit for someone who died during twilight?A: There are two issues: The memorial and reciting kaddish. The memorial is visiting the grave, having a meal or learning Torah. It is possible to perform these acts another day. If the yahrzeit fell on Shabbat, these acts would be on a different day regardless. The memorials are based on the convenience of the family, and they are not even obligatory. Regarding kaddish, there is no need to be strict and recite it on two days. It can be recited the day before or after. It does not matter, either option is good.

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