On 06/05/2014 06:19 PM, Zak Rogoff wrote:
Hi all,

https://EmailSelfDefense.fsf.org

We just released this guide to GnuPG with Enigmail and are quite happy
with it. Thanks to all of you who gave feedback on the draft. More is
welcome :).

I appreciate clear guides like this one.

I have one criticism and one comment.

Criticism:
You do not adequately warn current webmail users about the inconvenience of pinning the content of their encrypted messages to a single machine. Every encrypted message they send or receive is a message they cannot access on their other devices. This could lead to a self-defeating process where the more work a non-technical (or not very technical) user does to encrypt the content of their messages, the harder it becomes for them to generally access or manage their data. And because the setup doesn't protect them from metadata surveillance (and even leaks data through the subject line as you point out), there is likely to be a fairly low threshold before the user just abandons the setup altogether.

I read Richard Stallman's recent blog, I would agree that inconvenience is clearly a separate and less pressing issue than oppression. Nevertheless, there ought to be a clear warning that following this guide _will_ degrade the very ease of access which popular cloud services provide. Without that, users of the system will suffer undue frustration. Non-technical users-- even ones who fully grasp the wide chasm between inconvenience and oppression-- don't know how difficult it is to do decentralized and secure syncing of their data. All they will know is that it looks and feels more and more constrained, like using the internet a decade ago (you even use the word "desktop" in one of the initial paragraphs).

Comment:
It would be neat if you encouraged the users to exchange keys with someone who is already using a PGP key in a free software community (Debian, etc.). Like a reverse outreach program:

Dear Expert,
Greetings! I just read a tutorial on using PGP for encrypted mail, and I heard from a friend that you know a lot about computers. I read in the news that the internet is sorta broken atm, so if you wouldn't mind helping me use my computer safely and securely until y'all get this mess fixed I'd sure appreciate it. Let's get together and exchange keys.
Best,
Normal Person

-Jonathan
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