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I am contemplating taking the February LSAT to (ideally) supplement my application file and increase my chances of getting off the waiting lists I have been put on already (UVA and Penn).

Does anyone know if:
(1) This is something that could help supplement my application assuming it was a higher score?
(2) What effect my registering for an additional LSAT date could have on the admissions decisions that are still pending?

I'm in the same boat. I don't see any downsides to retaking, especially if you're already accepted to a school you would be happy attending. The schools you are waitlisted at will definitely look at the new score. Schools that you are borderline with will probably hold your application until they get your score, but scoring higher would surely help.

i thought about this but most schools explicitly state they only consider up to December. plus it will cause an auto delay at the schools your pending on. And theres always a chance you stay teh same or go down in which case they will most certainly not let you in off the WL...

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Just a follow-up:

So I registered for the February LSAT and I still have 5 decisions pending. I recall reading somewhere on the forum of someone who turned in an application prior to a December retake and that the school contacted them stating that their application will be held. Does anyone know if the schools are all notified through LSAC of my registration for the February LSAT? Should I write to them to ask them to hold my admissions decision for my score? How should I approach schools like NYU that do not accept February scores?

My inclination is to write a LOCI that states I have also registered for the February LSAT in an effort to provide the school with more information about my candidacy.

in all honestly, i would recommend waiting a cycle for people hoping for a february lsat boost, its just too late for you to fully benefit. to answer you question, LOCI and call admissions office everywhere you are pending to discuss.