Kevin and I have racked our brains, small as they are, to come up with a way to Bcc the Highrise Dropbox in an automated way. We’ve spent countless hours fiddling with Apple’s Automator, and we’re still at ground zero on this. Until now that is…

While doing a little more research late last week on the topic of automatically Bcc’ing the Highrise Dropbox, I finally came across a hack for Apple Mail that does just this. I’d like to offer a big shoutout to Travis Vocino of Vocino Labs for originally sharing this out. The hack does of course require that you are comfortable with using the terminal application and entering information via the command line. ***Please read the entire post before performing the hack.*** Here is the hack:

1. Open Terminal.app
2. $ defaults read com.apple.mail UserHeaders
3. If nothing shows up, you don’t currently have anything set and you should be golden to move to the next step.
4. $ defaults write com.apple.mail UserHeaders '{"BCC" = "dropbox@YOURDROP.highrisehq.com"; }'
5. Restart Mail.app

When I first completed the hack I was quite excited. I restarted Mail as instructed and quickly used the hot key combination command+n to create a new mail message. I was quite disappointed when the new mail message opened up and I didn’t see anything in the Bcc field. My first assumption was that perhaps since I was running a newer version of mail that the hack didn’t work. Fortunately, my trusty sidekick and business partner, Kevin Gilbert, decided to go ahead and send some test emails anyway. What we found was that the hack did in fact work, it just doesn’t place anything in the Bcc field.

A word of warning, if you use the Bcc field a lot or with any regularity, be aware that performing this hack will cause Apple Mail to only send a Bcc to the Highrise Dropbox, regardless of what you enter manually in the Bcc field. In plain English, executing this hack means that you cannot Bcc any other contact besides the Highrise Dropbox even if you manually type their email address into the Bcc field.

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