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I am working for a company that engages in unethical business practices with a customer. I need to send an anonymous email to the labor board and the customer. I need to keep my identity a secret, but the contents of the email do not need to be secret. I also need to be able to respond to replies. Is the following safe?

  1. Head to an open wifi that I have never used before
  2. Switch on VPN (which provider is best for anonymity?)
  3. Open Tor and sign up for an email provider and send the email
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  1. When you go to the place with the open wifi, you should additionally check if the place is physically secure. This means no cameras, no people who could shoulder-surf etc. Furthermore if you connect with your own hardware to that WIfi, keep in mind that you leave some information (MAC address etc.). So using other hardware might be a good thing.
  2. VPN is not really needed. Please read https://github.com/epidemics-scepticism/writing/blob/master/misconception.md#vpns
  3. You should use a distribution which anonymizes all your traffic, like tails.
  4. Please keep in mind that you also leave some non-technical information:
    • your style of writing: Usually people have quite individual styles and if there are enough probes of your writing style available, it might be possible to track you down.
    • specific information about the case: Think about how many people can know about the case you want to report. This are the possible suspects. If this set is rather small, it could also be possible to track you down.

Stay safe.

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  • Thank you for your help. Is it possible to hide the wifi network I am using?
    – jkwon
    Commented Sep 8, 2017 at 17:43
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That sounds secure to me. When you sign up for an email service, make sure not to give any identifying information away. You'll find that a lot of email providers require you to give your phone number, so you can't use those. A VPN is not necessary, unless you're looking to hide the fact you're using the tor network, or the network you're using blocks tor connections. If you're looking for a good VPN provider, IVPN is very privacy & security oriented.

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Tor is your best bet.

There are free email providers that you can access over Tor. By using their webmail client, over Tor, they will not know your real IP address - only the IP address of the last node in the Tor chain.

Several of these services exist. Protonmail and Tutanota are the two most popular services. Secmail.pro and nextlinemail.com are two additional services.

Disclaimer: I'm the operator of nextlinemail

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