01Make a List
Make a list of all your W-2s, 1099s, and other tax-related documents. This accomplishes two things: You'll know exactly what you sent to your accountant and if something gets lost and doesn't arrive at the other end, you can identify what it was. You'll also have the start of a checklist for next year's tax preparation.
02Make Backup Copies
If you're transmitting the actual paper copies of your tax documents, do yourself a favor and copy them all first. That way you won't be without critical information if they do indeed get lost. You can photocopy them or scan them into image or PDF files, then save them on your PC and on a flash drive as an added precaution. However you do it, make sure you have a backup copy before sending the paperwork to your accountant.
03The Best Option Is Hand Delivery
When a spy wants to ensure that a document is delivered to the right person at the right time in the movies, he delivers it in person. He doesn't take the chance that it might be intercepted.
You can put this old-school tactic to work for you by personally delivering your tax documents to your accountant if at all possible. At the very least, hand them to his assistant, secretary, receptionist, or other office personnel. This eliminates any risk that they'll get lost in transmission or be intercepted by eavesdroppers.
04Mailing Your Documents
Mail delivery is pretty secure and is probably your second best option if you live in Philadelphia and your accountant is in Pittsburgh so hand delivery just isn't an option.
Your documents are protected from casual eavesdropping by virtue of being wrapped in an envelope. Opening someone else's mail is a crime, at least in the U.S., and while that might not deter a determined criminal, at least there are laws on the books to punish offenders.
That said, documents can and sometimes do become lost or damaged in the mail, so it might be a good idea to send those backup copies you made rather than the originals. And consider using some form of delivery or signature confirmation, or bypass the U.S. Postal Service entirely and use a delivery service instead such as Federal Express or UPS.
05Faxing Your Documents
Faxing documents to your accountant can be a quick way to deliver them and it's relatively secure. As long as the accountant's phone line isn't tapped, chances are good that your transmission won't be intercepted by identity thieves. But be absolutely sure that you have the fax number correct.
There are a few downsides. Faxed documents can sometimes hard to read and the last thing a tax professional wants to do is sit there guessing whether a number is a six or an eight or taking additional time to call you to find out. Faxing works best if you just need to send a few pages. For longer documents and especially for documents containing information on both sides of a page, faxing might not be the best solution.
06If You Must Use Email ...
Email is convenient and fast, but it can offer about as much security as a postcard. Unless you take precautions, any network carrier can see the contents of your email and view your attachments. Whether they're paying attention and actually tracking the contents is beside the point—there's still the potential.
Check into whether your accountant uses secure file exchange software such as LeapFile. Many do, according to Chip Capelli, an accountant located in Provincetown, Massachusetts, and this can be a game changer.
At the very least, place your tax documents inside an encrypted wrapper such as a password-protected DOC, PDF, or ZIP file. "Scan everything to a PDF and then password protect it," Capelli advises. Never send information you want to keep private, such as your Social Security number, as plain text in the body of your email message. What if you accidentally send the message to the wrong address or your email is scanned and the data harvested by your service provider? Taking precautionary steps to secure your tax documents help protect your finances.
The Best Secure Ways to Send Tax Documents to Your Accountant
Resist the Urge to Use Email
In the age of the Internet, it's becoming more and more common at tax time for people to enlist the help of professionals and accountants who might be at an inconvenient distance. It can be tempting to simply email the necessary information, but that's not the best idea.
You'll want to make sure that your tax documents are delivered to your certified public accountant, enrolled agent, or other tax professional in the most secure and reliable way possible. Tax documents contain highly sensitive information like your name, address, Social Security numbers for you and your dependents, how much money you earn, and where you bank. And that's just for starters. If that data falls into the wrong hands, you could end up being a victim of identity theft.
Here are some tips for making sure your documents and your data arrive at their destination intact and secure.
Updated January 2018 by Beverly Bird