The (Imperfect) Art of Sending Sensitive Stuff

Securer file sharing with Dropbox « practically efficient

Zip your files

Put the zip file in your Dropbox ‘Public’ folder

Email the file link, not the file

Great advice on sending sensitive stuff via Dropbox . And pretty close to what I do. With this handful of paranoid additions involving chaos and automation:

Parent Folder. in your “~/Dropbox/Public” folder, create a new folder with a sensible name like, “seekritstuff”
James Bond Naming. Keep a sane name for the uncompressed source doc you’re sending (say, “2010_income.txt”), but rename the zipped version of that file with a random name
- e.g., something like, “I8-H~*gY{4%u.zip”
- TIP: 1password can generate a “password”-style string that makes a swell file name
- Maybe an unnecessary step. But it does makes the file name way harder to just guess
Hazel help. Most Important. Create a Hazel rule for “~/Dropbox/Public/seekritstuff” that automatically moves any file it contains to a local/non-Dropbox folder on your Mac n days or hours after “Date Added”
- Mine’s set to 36 hours, but your setting can be whatever suits you and your recipients
Two-steppin’. Yes, send your recipient the link to that zipped file (NOT the actual file)—but do so in a separate and obscure-looking email that makes no reference to either previous emails or the link’s contents.
- Viz.
  
  SUBJECT: thing for you
  B—
  here’s that thing
  http://i-0.us/e4wQcw
  call or text me with questions
  
  /m
- Even better still? Send that link to a different email address for that person, or TEXT them the URL
In general? Just never hurts to mix it up. All of it.

It’s a start.

Like anything that touches an open network—and most especially anything that touches email—it’s a solution that’s far from perfect. But, to my mind, it feels a little safer than crap like sending plaintext via email.

Seriously. My mind is boggled by how many people throw sensitive stuff around in email to complete strangers—the equivalent of writing a password on a postcard. Then pinning it to the corkboard in the laundromat. Insane.