Does anyone know of a source that discusses everyone's entering Israel at t'chiyas hamesim and the ban on Moshe's entering Israel in light of one another (and, preferably, attempts to reconcile them)?

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It's not really a contradiction. The ban wasn't everlasting (i.e. it didn't extend to the end of time and resurrection), but precluded Moshe Rabbeinu from entering Israel in his lifetime.

The Midrash Rabbah tells us that Moshe did not enter the land for the sake of the generation that died in the desert.

Midrash Rabbah V'Eschanan (words in brackets my addition):

כי לא תעבור את הירדן הזה. אמר לו הקב"ה למשה אם אתה נקבר כאן אצלן בזכותך הן באין עמך


כך אמר לו הקב"ה למשה אם נקבר אתה אצלם במדבר הן באים בזכותך ואת בא בראשם שנאמר (דברים לג) וירא ראשית לו וגו' ויתא ראשי עם:

For you shall not cross this Jordan [river]: G-d said to Moshe, "If you will be buried here with them, in your merit they will come with you [into the land]" ... So G-d said to Moshe, "If you will be buried with them in the desert, the will enter in your merit, and you will lead them. As it says in the passuk...(Devarim 33:21)"

The Or Hachayim on Devarim 33:21 brings this idea as well, and uses the phrase "to bring the generation of the desert into the World to Come".

Although it could be argued that both of those sources could technically be interpreted to mean that Moshe would bring them into Gan Eden (as opposed to into the land of Israel with the Resurrection), the Lev Chaim (Part 1, Chapter 32) quotes a Midrash Hane'elam that says explicitly that "Why did Moshe pass away outside the Land of Israel? To show the nations of the world, the same way G-d will resurrect Moshe, he will resurrect his whole generation, in the merit of their receiving of the Torah".

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    I haven't researched this, but that "ha-yarden ha-zeh" seems significant to me -- Moshe doesn't get to cross this Yarden to enter the land, but in the future things can be different. Dec 19, 2011 at 19:27

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