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Apologies in advance, but here we go:

1. Do people send out emails or hard copy applications when they mass-mail judges/firms/government agencies for 1L summer employment? If you want to tailor a letter to some firms before 2L OCI, should you send out everything by snail mail?

2. I'm trying to put together a list of judges that I want to contact for 1L summer, but I can't find their contact information...only their bios and stuff. Where should I look? Am I supposed to contact them directly or some clerk/assistant?

Judges- Paper.
Everyone else (just about)- email.

Your school will tell you how. You aren't sending anything until December anyway (just about).

What exactly were you planning on sending out a month before starting law school?

Cool your jets bro, you're not technically allowed to send anything out before November 1st anyways and your career services office will hook you up with all the info you need

Not planning to send out anything, just wanted to get contact information/general cover letter drafts ready so I didn't have to do it during the semester.

You can do them on your computer and then when you find out what format they prefer, email or print and mail as appropriate. HTH

Your career services will have books with addresses of every judge, and point you to online resources with the information as well.