The (Imperfect) Art of Sending Sensitive Stuff

merlin:

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 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://db.tt/jr0eqAK
      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.

  1. File -> Print. Click the PDF button. Select “Save as PDF”
  2. On the Save dialog, click “Security Options”
  3. Check “Require password to open document”. Use a good password from a password generator. Use the googles.
  4. Save document.
  5. Email document.
  6. Text message or Phone a Friend with password.