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There are minhagim that seemingly go against halacha. I want to know essays or sources that cover this age-old debate.

It is my view that these minhagim are of three types:

  1. Machlokes of major poskim in which the minhag, although not following the "correct" halacha, still follows a major opinion. For example, putting on tefillin on Chol Hamoed which is a machlokes between the mechaber and the rema. Chasidim and Gaon followers (in Israel) to the most part don't put on tefillin, which goes against the rema, but nevertheless thay have the mechaber to rely on
  2. Minhagim that go against halacha and don't have any reason other than "minhag haolam". For example, not sleeping in the succah, for which the rema and many other poskim try to bring heterim for, but it is obviously just a limud zechus and not an outright heter. (I am excluding the chabad minhag of not sleeping in the succah, which has a reason and as such fits into the next category. Also excluded are real מצטערים)
  3. Minhagim that go against halacha and have no "real" halachic backing but nevertheless have a reason, maybe mystical, behind them. For example, not sitting in the succah on שמיני עצרת outside Israel, or the chabad minhag of never sleeping in the succah, which are outright against halacha, but the minhag has been around for generations with great Tzaddikim following it.
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    This interesting question was getting votes to close because it was asking 2 questions. So I edited it to reduce it to one question and added a little clarification. The OP can always reject my edit if he wishes. Commented Oct 12, 2022 at 20:19
  • Chabad not sleeping in sukkah was started by the last Rebbe, so not generations. And it was criticized by all the people who criticize him.
    – N.T.
    Commented Oct 12, 2022 at 21:01
  • @N.T. based on a conversation the lubavitcher rebbe had with a rav from yerushalaim (printed in a teshuva sefer), the rebbe claimed that this minhag is around for a long time. In any case, this was only an example, and still is one, for a minhag that is followed for a reason and not just because minhag haolam is to do it
    – Yoreinu
    Commented Oct 13, 2022 at 22:15
  • The starting point for any conversation such as this, is the Pri Chadash in OC 496:2 where he has 4 pages discussing the topic and covers all your questions and then some
    – Chatzkel
    Commented Oct 16, 2022 at 1:52

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