How To Send Sensitive Information Online
Going Paperless and Sending Financial Documents

What You'll Find In This Chat ...

Let's chat about good bookkeeping practices.
  • How Email Works
  • I Have Nothing To Hide
  • What You Can Do
  • Online Best Practice Options
Brooks Duncan, Mr. PaperlessMr. Paperless

by Brooks Duncan, CMA
Author of Paperless Document Organization Guide

Brooks is devoted to helping individuals and small businesses go paperless by turning piles of paper into an organized, electronic system.

On more than one occasion I have been referred to as "Mr. Paperless", so I try to follow my own advice whenever possible. This includes signing up for paperless billing from my utility providers.

Imagine my dismay when I received the first paperless bill from my gas company, and it was sent as a PDF attachment in an e-mail.

Why is this a bad thing? Isn't it more convenient this way? 

Convenient yes, but sending personal sensitive information in an e-mail is not a good idea at all. Let's discuss why that is.

How E-Mail Works

When you send an e-mail, you might think that your e-mail system connects to your recipient's e-mail system and delivers the message. You might even think that things are secure because you log into webmail and you have that little lock symbol in your browser.

Those are both logical assumptions, but they are not quite right. Here is how it actually works:

Why it is a bad idea to send sensitive information by unencrypted email.

When you hit send on that e-mail message, it gets sent from your provider to a central server somewhere. Then that server hands the message off to another server somewhere, and so on and so on until it gets to your recipient's server. It could take quite a few hops along the way.

These messages are sent in "clear text", which means anyone with access to any of those servers, or anyone listening in at any point along the way, has complete access to your message.

Even worse, those messages can sit around on any of those servers for months. Even if you or your recipient deletes the e-mail, it may still be out there somewhere.

“But I Have Nothing To Hide”

Frankly, I don't care if some hacker or bored system admin reads my wife asking me to go to the grocery store to buy kale. However, if I was buying a house or applying for a loan, I sure as heck would not want those documents sitting around on some mail server in Manitoba or Idaho.

Identity theft is a big enough problem as it is without us making it easy for them.

What You Can Do
Online Best Practice Options

Send sensitive information by encrypted email.

You can still use e-mail to communicate private sensitive information, but you just need to be a bit more smart about it. Here are some options:

  1. Use a cloud service like Dropbox, Evernote, or Box to host your document and create a private link. If your e-mail is intercepted the third party would still have access to the message and the link, but you can remove the file or shared access as soon as the recipient has downloaded it. Your exposure time is greatly reduced.
  2. Use a private cloud device like the Connected Data Transporter. This is similar to option 1, but your data is never hosted on an external service. You control it.
  3. Use a secure service like E-Courier. This allows much greater control over access to sensitive information, and your documents are "shredded" after a certain period; the shredding deadline is set by you.
  4. Use encryption or password protection: You can encrypt or password protect the documents before sending. This is the most secure, but you need a way to tell the other person how to decrypt the document which can add friction to the process.

Taking a little time up front to protect yourself with e-mail will make your private sensitive information much more secure. Now if only I can convince my gas company of this.

Brooks has published the following paperless tools ...

To learn how to turn your piles of paper into an organized, electronic filing system, click here. Pricing starts at $15.

The Unofficial ScanSnap Setup Guide takes the pain involved with setting up your scanner. Skip your Starbucks coffee today. Ease your setup pain for $5.

Learn how to get your Mac to name and file your documents automatically for you in the Go Paperless With Hazel Webcast. View this very affordable webcast for $10.

Going Paperless and Sending Financial Documents

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