How Can I Securely Submit Confidential Tax Documents to My Tax Filler?

Dear Lifehacker, Tax season is in full swing, I’m ready to send my documents to my tax filler and I’m wondering: In this digital age, how can I safely (and free) submit my tax documents to my CPA?

Signature, Sensitive insecurity

Blast From The Past is a weekly feature on Lifehacker in which we bring old but still relevant posts to life for your reading and hacking enjoyment. This week, ahead of tax day, we remind you of safety.

Dear SI! The personal and confidential information contained in your tax filings is an identity thief’s dream: names, addresses, social security numbers, banking information, and so on. This is the most confidential packet of information that most of us send out in a year, and, you are right, taking a few steps to keep the information in it safe is the least you can do!

So how do you keep it safe? You have several options, some of which I’ll highlight below:

Personal transmission

For safety’s sake, it’s hard to beat the old school in person. It’s not the most compelling option in the digital age, but there is certainly something exciting about transferring top-secret documents. Take a briefcase with you and make a spy movie out of it. Or not.

The fact is that there is no safer way of transferring documents than physically transferring documents into the hands of the tax preparer. You can make it digital, transfer it in person if you want – let’s say you scanned your documents and put them on a CD or better yet , a password-encrypted USB drive .

The important thing is this: there are no personally involved intermediaries. There is no middleman between you and your originator, during which some protection, unencrypted transmission method, or some other unknown variable could reveal your sensitive data. This is your hand to the tax preparer. There is nothing safer than this.

Digital alternatives

If for some reason transferring in person is not an option, and you really want to send confidential documents over the Internet, you still have options to make this transfer more secure. Here are a few things to keep in mind:

  • Do not send confidential documents by email. It might sound confidential, but even if you are using an email account that downloads attachments over a more secure HTTPS connection like Gmail, you have no control over the recipient’s server and they can download your attachment over an unencrypted HTTP connection. Now, let’s say they did it from a public Wi-Fi network. Everything has become very insecure.
  • If you are set to transfer files digitally, you should encrypt them (which you can do with one of these tools ). For example, with a tool like 7-zip , you can create a password protected archive (with super strong AES-256 encryption). You will still need to give your tax officer the password for your encrypted archive, which you don’t want to do via email for the same reason you don’t want to send files as attachments.
  • Share your documents using an encrypted file sharing service. Many file sharing services offer some sort of encrypted transfer for file sharing. One of them is Dropbox. Let’s say you and your seasoned tax officer have created a shared Dropbox folder. Anything you put in this folder will be encrypted and moved from your Dropbox folder to the Dropbox servers to your tax officer’s Dropbox folder. (One notable exception: if any of you access files from the Dropbox mobile app, your file names will be transferred unencrypted , which can actually be a problem if the document names contain sensitive information.) But now you also have there is a copy. your confidential files on other people’s servers, and you must fully trust this service and its security. You can also put the file in your Dropbox public folder, send your presenter a link to it (make sure you add the ‘s’ to the end of the ‘http’ in the link you share – it wasn’t there by default for me), and then remove it from Dropbox as soon as it downloads it. Again, there are weak points, but still pretty reliable.

The above list of considerations does not exhaust your options for secure digital transfer or things you might want to consider, but it does give you an idea of ​​the complexity that arises once you migrate your transfers to the purely digital realm. It’s not that you cannot securely transfer documents digitally by any means, but if you have the ability to do it in person, this is truly your best bet.

Sounds a little doomsday, doesn’t it?

If you send your tax documents in plain text by email, will your identity be stolen? Probably no. I’m sure a lot of people do this every day, and it doesn’t make them worse. But if your hatred of tin foil is securely attached, as we do, there is no reason to put yourself at that risk.

This is why, despite some fairly reasonable digital options, we still recommend handing over documents in person. An ounce of prevention and all that.

Love, life hacker

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