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I just finished sophomore year and am going to apply during my gap year. Should I ask a LOR now when the professor has a fresher memory of me or later closer to when I apply?

(Also my school uses a specific portal that only applicants of the upcoming cycle can use to collect LORs, but can I just use interfolio myself then upload it manually?)
You should still be able to use Interfolio unless your school portal includes an committee letter of sorts. Otherwise, Interfolio Gould be fine. I see nothing wrong with asking now with a due date in September? As long as they are dated within the year prior to your submission it shouldn’t matter.
 
I just finished sophomore year and am going to apply during my gap year. Should I ask a LOR now when the professor has a fresher memory of me or later closer to when I apply?

(Also my school uses a specific portal that only applicants of the upcoming cycle can use to collect LORs, but can I just use interfolio myself then upload it manually?)
I'd go with option 3 if possible, which is to maintain a relationship with that professor over the next couple years (maybe do research with them or take more of their courses) and then ask for a letter closer to game time. That way s/he will be able to write a much stronger and better-informed letter.
 
You should still be able to use Interfolio unless your school portal includes an committee letter of sorts. Otherwise, Interfolio Gould be fine. I see nothing wrong with asking now with a due date in September? As long as they are dated within the year prior to your submission it shouldn’t matter.

Yes there will be a committee letter involved. And the due date would be 1+ year from now, not this September (rising junior not senior so not applying this cycle).
 
Sounds like a solid idea. However the professor doesn’t offer any courses besides the one I took, and only has graduate students in his lab.
Total bummer. Could you try for a job as his TA? Or be the persistent undergrad who manages to become the exception to his "grad students only" policy?
 
Sounds like a solid idea. However the professor doesn’t offer any courses besides the one I took, and only has graduate students in his lab.
I haven’t had a class with one of my LOR writer’s for a year now, but every time we pass in the hall we have brief casual conversation about hunting or our children etc etc. That minimal interaction seems to have been enough to maintain our relationship.

You can find a way!
 
I just asked for my letters after the classes. That way they remembered me. If you legitimately want to TA or continue your connection than you could do that but I wouldn't force yourself to just for the purpose of a letter
 
My son (rising junior) asked one of his instructors (non science) for LOR for next year that way she will remember him.
 
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