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I'm a 3L applying to some COA clerkships. I have a district clerkship starting in 2021. Can I update my OSCAR profile to indicate I have "law clerk experience" even though my position starts in the fall, and if not, when is that kosher?

interested in this as well

If you're applying for 2022 or later positions, I'd say it's fair to check this box. By the time you start, you would already have clerked. I think the question is meant to tease out whether or not you have clerked before once you start clerking for this judge.

I would not check this box if I was applying for 2020- positions.

I am in the exact same position as OP (district clerkship lined up for '21, applying for COA '22) and checked the box, FWIW. I'll have clerkship experience by the time I start in '22. Doesn't seem like a big deal either way though since your cover letter would indicate your '21 clerkship anyway.

I'd check it as long as you'll have law clerk experience by the time you get to the positions you're currently applying for: that's almost certainly the thing the judge cares about. If the judge wants to know the full details and timing, he can open your application, but, if it's something judges can sort/filter by and you don't have that box checked, your application might never be looked at by anyone even though you'll have that experience by the time you start.