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Do you all think that applying to transfer (just for context, this would be going from a T20 to Y/H/S) hurts you at your current school if you end up not getting accepted or deciding not to transfer? Since at least some of the faculty would be aware of your attempt, do you think they would be less likely to help you line-up clerkships, etc. in your remaining years?

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I genuinely don't think so. You can always paint it as you were just looking around at options and decided that you really like your current school, are happy with your prospects, and want to stay. Thats quite the compliment to the school, especially if you genuinely have the option to make a move up. Just go through your transfer process tactfully and quietly. Don't make it known to all your classmates that you are trying to transfer. Keep it quiet as best as possible. To the extent you speak with professors, do it respectfully and portray things in the best light.

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Not at all. I applied to transfer. Ended up staying. The same professors who wrote my transfer LORs wrote clerkship LORs for me and my school is pushing me hard for a clerkship. I kept it under wraps from my classmates (almost all of them) because I didn't want to say anything until I made a decision. But it didn't hurt me at all when it came to my school and professors.(or classmates...but like I said, I didn't tell most of them)

Thanks for the input!