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I've been told that it is a good idea to send targeted applications over the summer to firms that aren't coming to OCI at my school. When is the ideal time to do so?

I've heard early August. My plan is to have my mass mailing stuff ready to go out by the time OCI starts.

I would personally do the mass mails somewhere in the July 25-August 1st window. Others may do it slightly earlier, and some may do it slightly later. If it were a firm in a city where I'll be before OCI (either working or visiting briefly)I, I would send on July 15th and say that I'm available to come in to their office to interview anytime from August 1 until August 15, or whichever dates are applicable. I think it may be beneficial to give them about a two week window to prepare for in-office interviews instead of having recruiting decide not to scramble to put something together for that upcoming week.

I would also send another round of emails to firms I bid on and didn't get as soon as that information is out. Say that you're very interested and would love to see if you can schedule an interview with someone in their hospitality suite (find out if they have one), during a break, or after the official end of the day. Some will respond in the negative, others will not respond, still others will tell you they'll put you on their waitlist for any cancellations, but a few may agree. I picked up a couple interviews that way, and one turned into an offer.

A week or two before OCI starts.

I plan on mailing hometown firms as soon as journal results come out on July 21.

How much are you guys planning on changing your cover letters? Mine seemed to work pretty well for mass-mailings for 1L gigs, but I'll be sending it to a lot of the same firms for 2L as I did for 1L. I don't want them to think that I don't care enough to change my cover letter, but I also don't have the slightest clue how I need to change it.