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I have heard that there are people who keep Shabbos till Tuesday. I would like to understand how that works practically. A few examples of puzzling situations:

  1. What shmoneh esrei does such a person daven Sunday morning
  2. Does this person include retezei in bentching? Assuming he does, would this person have to repeat bentching if it was omitted?
  3. How does this not violate the prohibition of adding to a mitzvah?
  4. Which day of the omer would he count Sunday evening?
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  • related judaism.stackexchange.com/q/13922/759
    – Double AA ♦
    Commented Mar 20, 2013 at 5:13
  • 2
    I don't think anybody actually does this.
    – Daniel
    Commented Mar 20, 2013 at 6:01
  • I don't think they bentch since they can't eat until they say Havdalah, and if they say Havdalah it's not Shabbos for them anymore.
    – Ariel
    Commented Mar 20, 2013 at 6:28
  • I heard that the Jews in Japan during WWII had issues with the location of the Jewish date line and, as a precaution, kept two days of Shabbos and even two days of Yom Kippur. But I've never heard of anyone holding by Shabbos thru Tuesday.
    – Bruce James
    Commented Mar 20, 2013 at 13:09

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I'm not sure I believe the source you quote, since the Amshinover Rebbe is known for "running late" but not for skipping days. But here are some answers to your questions:

What shmoneh esrei does such a person daven Sunday morning

Most people daven on Motzai Shabbat before they have ended Shabbat, yet they say the weekday Amida.

One may actually daven Maariv on Motzai Shabbat before "3 stars come out"; some people do this regularly (e.g. "keep" Rabbeinu Tam, yet daven earlier), others do so on Chanuka so as to light as soon as possible. Either way, on Motzai Shabbay one always davens the weekday Amida.

So too on Sunday morning he would say the weekday Amida.

Does this person include retezei in bentching? Assuming he does, would this person have to repeat bentching if it was omitted?

One is not allowed to eat after sunset on Shabbat afternoon before Havdala (Kitzur SA 96:4), so we must be talking about somebody who started eating on Shabbat. This person needs to say Retzei.

If he forgot, he wouldn't repeat the bentching , like anybody else who forgot Retzei at Seuda Shlishit. (Kitzur SA 44:13)

How does this not violate the prohibition of adding to a mitzvah?

Tosefet Shabbat is a Mitzva; so he's simply stretching an existing Mitzva.

Which day of the omer would he count Sunday evening?

By now you already know what I'm going to answer: He would count the correct count.

Reminder: One who forgot, couldn't or purposely didn't make Havdala on Motzai Shabbat, may do so until the end of Tuesday [afternoon]. (Kitzur SA 96:15)

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