Securing and sending documents for job and taxes

Since applying for jobs and filing taxes is a virtual affair, how do you secure your documents so everyone doesn’t see your social security number and other sensitive information?

With switching jobs, I had to send multiple documents including my driver’s license, salary information, SSN, beneficiary details, birthdate, address, and lots of other personal details. Not information you just want floating around out there.

So, how do you deliver such information?

Create a Secure Volume:

If the other person has a Mac, the easiest thing to do is use a password protected DMG file. It only takes a moment to create and you can drop all your files inside.

To work cross platform, if they’re willing to spend a few moments installing software, VeraCrypt creates a password protected volume that works on both Mac and Windows.

Another alternative is the password protected Zip file. Using tools like Keka, BetterZip, or 7Zip, add files to the archive, set the password and get it ready to transfer. The format will be compatible across systems. You need a true zip tool though, not just an extractor.

Transfer securely:

Now that you have a password protected file, how do you send it? I chose to use the Dropbox Secure Transfer. This worked really well, is free, and allows files of 100MB. That should be more than enough unless you literally have hundreds of documents to include.

Dropbox can send an email link to the files, which adds another layer of obscurity since that link won’t show in your mailbox. When the file is downloaded, you get notified so can keep track of who accesses it. You don’t have to worry about server attachment limits either.

To send the password, use a site like The password can be viewed once then is deleted. Once it has been seen, the link no longer works. Using this method and sending file links through Dropbox, there is a password, but no reference to what it goes to. Only the person you are working with has both pieces.

Local Encryption:

Local encryption for your tax information is just as important. If you scan documents such as W2 information, and beneficiary details, those can easily be stored in a password protected DMG or a VeraCrypt vault.

If you need to obscure one or two pieces of text information, Paranoia Text Encryption works extremely well. This would be a good choice for storing SSN inside DevonThink Office Pro for example. There is also an online version so you can send the encrypted text, and use to handle the decryption password.

If you want to take things further, you can use file and text encryption tools like CryptoEdit and AutoCrypt by Ecleti. AutoCrypt encrypts individual files, so each one could have a password. CryptoEdit creates encrypted text files.

So, you could encrypt multiple files, hash the passwords with Paranoia, then store them in a CryptoEdit text file. Might be a bit much for most cases, but it’s easily done if needed.

Those encrypted files could be stored in an encrypted volume for even more layers of security. It would take multiple and different passwords to get to the actual file.

There are tools like LastPass, Roboform, and others to handle passwords, but they are becoming increasingly expensive, have moved to subscriptions and are cloud based. Sometimes security should stay local. These other tools are far cheaper, and their yours. They work on your machine.

If you want to transfer files between machines using Dropbox or another cloud service, Cryptomator can turn them into secure volumes. I haven’t tried this yet, but it looks interesting.

At this point, there are quite a few ways to send secure documents. Using an encrypted Zip files, linking to it through Dropbox, and sending the password through worked quite well for me.

It's bad luck to be superstitious.
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