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I read the UPenn instructions, and it seems to me they only allow "an" (one) additional essay.
This is a problem because I was planning on writing both Why UPenn and an Addendum for my GPA.

"If you wish, you may write an additional essay on any of the following topics. These optional essays allow you an opportunity to provide the admissions committee with additional relevant information that you were not able to include in your personal statement. Please include the essay with your application by electronically attaching it to your application before submission through LSAC. You may answer more than one essay topic if you so choose. Include your name and LSAC account number on each page. Please limit any optional essay to one page, double spaced and title it appropriately."

Any thoughts?

"You may answer more than one essay topic if you so choose."

I'm doing the same thing, just using a different page for each essay with an appropriate title.

whambamthankyoumaam wrote:"You may answer more than one essay topic if you so choose."

I'm doing the same thing, just using a different page for each essay with an appropriate title.

Yep, if you can't upload multiple files, just create a single document with headers/page breaks.