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Today I had a firsthand experience on teaching someone how to use encrypted email. TL;DR: #PGP is in a horrible state of usability, yet this should not stop you from teaching other people about the principles of !privacy and security.
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@kzimmermann2 Which program did you use?
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@rugk@gnusocial.de Mozilla #Thunderbird with #Enigmail extension
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@kzimmermann2 I have hade great success with #Tails + persistent storage and #Thunderbird (Enigmail pre-installed).
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@mmn@social.umeahackerspace.se hardest part IMO wasn't even the interface or software stack (I used the same as yours minus Tails) but the lack of appreciation on why each component on the stack is necessary. Some responses sounded like "why do you need to install so many things? Other apps just work ootb." And they have a point in this case: whenever I show people encrypted XMPP, it abstracts so much that people don't even think about it.
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I don't know what you used but enigmail is pretty easy.
I suggest for your users to help them with this if needed:
https://emailselfdefense.fsf.org/en/