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yup have to update and upload
My letter writers all updated their LORs last year in May and August 2017 when I thought I was going to apply. While I didn't end up applying back then, I am applying this year. Should I tell my recommenders to update the letters yet again to this year's date?

I feel weird for asking them so many times, since they actually wrote these letters back in 2015-16 and have been updating them ever since 🙁
 
yes you should, even if it's just a change of date. Hopefully your writers won't be annoyed by this, since this can be done in a few minutes. I know at least one of my letter writers was happy to do it as I am submitting his letter for multiple occasions.
 
Wait, guys please answer this. Why do LORs have to be 2018 dated? I've some from professors from 2017 too, but I don't think they have a copy of those letters! Does AAMC only accept 2018 dated letters?

Note: I used interfolio.
 
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