How Can I Securely Send Sensitive Tax Docs to My Tax Preparer?

Dear Lifehacker,
Tax season is in full swing, I'm ready to send my documents to my tax preparer, and I'm wondering: In this digital age, how do I securely (and freely) send my tax docs to my CPA?

Signed,
Sensitive Insecurity

Blast from the past is a weekly feature at Lifehacker in which we revive old, but still relevant, posts for your reading and hacking pleasure. This week, with tax day on the way, we're reminding you to stay secure.

Dear SI,
The private and sensitive information contained in your tax documents are the stuff of an identity thief's dreams: Names, addresses, Social Security numbers, banking information, and so on. It's the most sensitive packet of information most of us send out all year, and, you're right, taking a few steps to ensure the security of the information therein is the least you can do! Imaged remixed from original by Kenny Louie.

So, how to keep it secure? You've got several options, a few of which I'll highlight below:

The In-Person Hand Off

For the sake of security, it's hard to beat the old-school, in-person hand off. It's not the most sexy of options in the digital age, but surely there's something titillating about a top-secret document hand off. Bring your briefcase and make it like a spy movie. Or don't.

The point is that there are no transmission methods more secure than physically placing your documents in the hand of your tax preparer. You can make it a digital, in-person hand off if you like—say you've scanned your documents and placed them on a CD, or better yet, a password-encrypted USB thumb drive.

The important thing is this: There's no middleman with an in-person hand off. There's no intermediary between you and your preparer during which some security breech, unencrypted transmission method, or otherwise unknown variable could expose your sensitive data. It's your hand to your tax preparer's. There's little more secure than that.

The Digital Alternatives

If for some reason an in-person hand off isn't an option and you really want to send your sensitive documents over the internet, you still have options for making that transfer more secure. Here are a few things to keep in mind:

• Don't send your sensitive documents over email. It may seem private, but even if you're using an email account that uploads attachments over a more secure HTTPS connection, like Gmail, you have no control over your recipient's server, and they may download your attachment from an unencrypted HTTP connection. Now say they did that from a public Wi-Fi network. Things just got very un-secure.
• If you're set on transferring the files digitally, you should encrypt them (which you can do using one of these tools). Using a tool like 7-zip, for example, you could create a password-protected archive (with super-strong AES-256 encryption). You would still need to give your tax preparer the password to your encrypted archive, which you wouldn't want to do over email for the same reason you wouldn't want to send the files as attachments.
• Share your documents using an encrypted file-sharing service. A lot of file-sharing services offer some sort of encrypted transmission for file sharing. One of those is Dropbox. Say you and your tech-savvy tax preparer set up a shared Dropbox folder. Anything you put in that folder would travel encrypted from your Dropbox folder to Dropbox's servers to your tax preparer's Dropbox folder. (One notable exception: If either of you access the files from a mobile Dropbox app, your file names would be transferred unencrypted, which actually could be a problem if the document names contain sensitive info.) But now you've also got a copy of your sensitive files on someone else's servers, and you have to place a lot of trust in that service and its security. You could also put the file in your public Dropbox folder, send your preparer a link to it (make sure you add the 's' to the end of the 'http' in the link you share—for me it wasn't there by default), and then delete it from Dropbox as soon as she downloads it. Again, has its weak points, but still pretty secure.

The list of considerations above doesn't exhaust your secure digital transfer options or things you may want to take into account, but it gives you an idea of the sort of complexity introduced as soon as you take your transfers to a purely digital realm. It's not that you can't securely transfer documents digitally by any means, but if you have the option to do it in person, it's really your best bet.

Sounds a little doomsday, doesn't it?

If you do send your tax documents unencrypted via email, will your identity be stolen? Probably not. I'm sure a lot of people do it every day and are none the worse off for it. But if you've got your tin foil hate securely strapped on like we do, there's no reason to expose yourself to that kind of risk.

That's why, despite some pretty reasonable digital options, we'd still recommend handing the docs off in person. An ounce of prevention and all that.

Love,
Lifehacker