How to Send and Receive Emails Anonymously?

Privacy Questions
1

Do I need to use as special email provider or client (I am using Proton webmail and the Thunderbird client), and why, i.e., what are the risk of using Outlook webmail or the client for example?

Do I need to use Tor and a VPN? I assume I only need to do this, if I do not trust Proton and my ISP.

My thoughts are using an email alias service like DuckDuckGo is enough, where my email will go from Proton > DuckDuckGo > Receiver, and vice versa.

I am not concerned with the email being encrypted, just that the receiver or any other parties are unable to determine the sender, and vice versa if I am the receiver.

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2

I’d create a new email account anonymously through Tor and I wouldn’t provide any personal information to that email provider. Use a random word generator for the name and address instead of thinking about a “random” one, as you might subconsciously pick words that someone that knows you might be able to relate them to you.

Remember to never access that email outside of Tor, to never use that email address for anything else and to be very careful that the contents of the email can’t be associated to you. Change your way of writing too so that the content doesn’t have “your tone”.

Then it doesn’t matter that the receiver knows the sender’s email address, because that email address doesn’t link back to you.

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3

Tuta/Tutanota just made a video walkthrough about how to create an anonymous email account with Tor on their YouTube channel. I would assume if you create an account this way and only access it through Tor, you could send and receive emails anonymously.

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4

Funny video, can I do it with Proton, or maybe Tuta is easier? Also, he doesn’t use a VPN or instruct people to, so I assume my ISP will see everything.

Also also, I am guessing Tor is not necessary if you trust Proton and DDG (only with your IP and other information you involuntarily give them).

5

I think the ISP would just see that you connect to the Tor network, but not the sites you visit. Your ISP would see you connect to your favorite VPN too.