How old can LOR's be? I have one from last year. Should I ask to have it reuploaded so the date is current?

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Oct 6, 2010
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Although this is often mentioned as SDN gospel, I don't know that it really matters. An LOR dated today but talking about your performance over a year ago isn't much different than a letter dated a year ago. If you've continued to work with this person and they can update the letter, that's obviously much better.

Still, it's probably best to ask them to update it. Some letter writers will not if they have no new experience with you since.
If you have new experiences, yes. If you don't... hit or miss. If you applied and didn't get in with the old letter, it's worth considering whether you should ask someone else for one.