How do I send an encrypted email with attachments from gmail?

November 14, 2013 8:40 AM

I know there are a variety of options out there, but I'm having a hard time sifting through the information myself.

I need to send a bunch of private documents to an institution. I can't mail it because it's very time sensitive (as in, needs to be received today). Fax and hand delivery aren't options. I really need to make sure this stuff is as confidential as possible. Other details:

- I have Internet explorer 9 and gmail. I'd rather not have to download anything else because that would require my administrator's permission and this is not work related (and can't wait until after work, unfortunately).

-The person I'm sending it to uses Outlook.

-I'd like to minimize work on their end as much as possible- a password or key is fine, but they shouldn't have to download software, addons, etc.

-nothing that has a time expiration (key is only good for one month, etc.)

Please assume I have no baseline knowledge about this stuff (because I don't)! Thank you.

posted by snarfles to Computers & Internet (7 answers total)

If you have Adobe Acrobat Pro, you can create an encrypted PDF of your documents and they can be deencrypted with a password that you can pass along in a different channel (i.e. over the phone, after you email the docs).
posted by scalespace at 8:47 AM on November 14, 2013

Zip files can be encrypted and require a password to open files (but not to see file names). Most archive programs support zip encryption, but depending on the recipient's operating system and installed software, there is a small chance they will have to download something.
posted by domnit at 8:49 AM on November 14, 2013

Er...apparently the file list is also encrypted. Sometimes?
posted by domnit at 8:50 AM on November 14, 2013

Apparently recent versions of Windows do not like password-protected zip files so much.
posted by domnit at 8:55 AM on November 14, 2013

You could put them in Google Drive and share the documents or folder. Google Drive doesn't let you encrypt on your desktop but transmission is encrypted and the other party has to verify they own the email address you identify them with before they have access to the shared folder or documents (maybe they have to have a Google account even if you don't identify them with a Gmail address though, I'm not sure). You can do something similar with Dropbox but I'm not sure that the other party has to verify their identity, and I'm not sure if they have to have a Dropbox account. And by the way, apparently Google is encrypting communication between their data centers now because it was revealed that the NSA had tapped into their fiber optic communications. So the only thing you might be concerned about is the documents not being encrypted when actually in Google's servers, and not actually encrypted by you.
posted by Dansaman at 12:54 PM on November 14, 2013

MS Office documents can be encrypted with a password.
posted by crocomancer at 4:47 AM on November 15, 2013

Hushmail?
posted by kuanes at 5:26 AM on November 15, 2013