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The Torah prohibits returning to Egypt (Deuteronomy 17:16, Sefer HaMitzvos Lo Sa'aseh § 46). The Sefer HaChinuch § 500 explains the reason for the prohibition is because the Egyptians are bad people, and Hashem doesn't want us to learn from their ways, considering He took us out from there in the first place.

Some want to explain that the Torah only forbade returning to Egypt via the path the Jews took in the wilderness during their 42 journeys (Divrei Shaul to Numbers 33:1,2, brought by the Toafos Re'eim to Sefer Yereim § 309 (303); see there his question on this). Some want to say the Ritva's understanding of the Yereim implies this as well. I've also heard some more recent divrei Torah quoting this idea. As an aside, this answers how the Rambam himself could live in Egypt (see here).

However, this seems extremely specific. Why would the Torah prohibit only this path, yet if a person is missing even one of the stops, it's totally fine to return to Egypt?

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It would be particularly offensive to God to return to Egypt using the very same path God chose to liberate us from there. It's like rubbing it in.

Aside: Having been born and raised in Egypt until forced out at age 18, and seeing Egypt judenrein (Jew-free) today for the first time in history, I believe the commandment not to live in Egypt ever again meant exactly what it said, and God always ultimately gets what He wants.

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  • You're simply saying its more offensive to live in Egypt by returning the same path, than to live there by going on a different path? The Torah only forbade the larger of the two offenses?
    – robev
    Jul 12, 2020 at 20:58
  • Yes. The later rabbis were trying to understand what rationale many gedolei Yisrael had for living in Egypt, and their speculations led to this explanation.
    – Maurice Mizrahi
    Jul 12, 2020 at 21:02
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    @Maurice I've read your interviews online and you have lived an amazing life so far (and may it continue to be amazing for many more years!) BUT I'm pretty sure this is the second time in Egyptian history that it has been left judenrein (see: the Torah, books Shemot-Devarim for more information regarding the first time all the Jews left Egypt)
    – יהושע ק
    Jul 12, 2020 at 22:09

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