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I went to law school for a few weeks a couple years back and am applying this fall after retaking. I assume I'll need a good standing letter from my first school. Should I send them an email with the list of schools I'm applying to, to send a letter. Or should I ask them for one and send it to the schools myself (is this even an option?)

You should have your old law school send them directly to the schools that you are applying to, the same as you would a transcript or LoR. I would absolutely not send the letter to the schools yourself.