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I have been requested to send a copy of a past year tax return to a US state office. I have been in contact with a tax official by email to send this copy through various means. This state is a few thousand miles away from my current residence.

What would be the most- to least- information-safe approaches to transmitting this tax document out of the following options this official currently has: email, fax, paper mail?

What I have done is the following:

  • I have asked the official about secure methods to send an electronic copy besides email, and the tax official responded that email is safe. I personally do not feel it is safe to send unencrypted messages of sensitive documents by email.

  • I have also looked into encrypting this document and sharing the decryption key over the phone with this tax official. But I got stuck currently on a good way to encrypt with my Debian Linux OS in a way that a tax official would be able to open.

I also have my own domain name that I could point the official to, and a cloud-provided server instance resolving requests to this domain as another option.

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    WRT, I have also looked into encrypting this document and sharing the decryption key over the phone with this tax official. But I got stuck currently on a good way to encrypt with my Debian Linux OS in a way that a tax official would be able to open. - I ran into the same problem, so I started this project on GitHub: github.com/meixler/web-browser-based-file-encryption-decryption
    – mti2935
    Commented Jan 1, 2022 at 0:36

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It depends on what risks you consider. Think, who can be interested in getting information about your taxes and what benefits will they get after getting such information. How much money are they ready to spend to get your information? If a lot, then it will be very hard to protect the information: They may intercept your paper post, install spying devices in your home, in your car etc. How big is probability that somebody is ready to spend such amount of money to get information about your taxes?

If you want to protect only against occasional accessing this information, then (arguably) the solutions may look as follows:

  1. Paper post.
  2. Encrypted PDF: Encryption with AES-256 is sufficiently strong, PDF readers are normally preinstalled on the most PCs, tablets, smartphones, so the receiver will no need to install any additional software.
  3. Encrypted ZIP: Encryption with AES-256 is sufficiently strong, but unzip tools are not as often preinstalled as PDF readers. Thus, depending on skills of the receiver, it may be more difficult to the receiver to unpack your ZIP.
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  • Interesting. What would be the motivation for putting paper post as a more information-secure option than an encrypted PDF, if that was the motivation?
    – shaky_dispute
    Commented Jan 2, 2022 at 4:25
  • @shaky_dispute: It depends on the receiver and their processes. If they prefer paper, then they may want to have your signature on the paper. Also the usability can be a problem for some users: Every time they open your encrypted PDF they would need to enter password. For this they would need to store your password somewhere. If they have no standard process for this, the password will be very likely lost and they may request you to send documents again. In such cases paper can be preferred.
    – mentallurg
    Commented Jan 2, 2022 at 16:11
  • AFAIK, the paper post is protected by federal laws. Said differently on a technical point of view it is by far the worst protection because anyone can open the envelope and read the content. But on a legal point of view it has the highest possible protection.
    – Serge Ballesta
    Commented Jan 31, 2022 at 8:31

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