On 12/07/13 13:38, Olav Seyfarth wrote:
> Hi Stefan,
>
> > For signatures it is maybe not so important, but what if you get an
> > important, encrypted, email? Then you will be unable to read it on your
> > phone unless the sender also encrypted it with your phone key.
>
> sure. On the other hand, the private key isn't safe on a mobile device.
It really is a matter of why you are using encryption. Random thieves
would not care about reading my encrypted mail (since it really contains
nothing of interest to them). Someone who did care about my mails
specifically could just as easily threaten to beat me up if I didn't
give them the key. Storing my key safely will not help me against that.
(I also don't care about email signatures. I don't worry about that).

Personally, I'm mostly concerned with mass surveillance, so if someone
happens to get my key, it doesn't matter much. What I'm hoping for is
that enough people use encryption that it discourages the powers that be
from even trying to implement email surveillance. That's why I try to
encrypt all my mail, no matter how mundane it is (and to aid this, I'm
developing a website where a user can pick her operating system and mail
client, and will then be given extremely simple point by point
instructions on how to make a PGP key and how to read/send encrypted
mail). I don't care much about the security of a specific key. If the
government manages to intercept one granny's cookie recipes it's not the
end of the world. If they do it to a million grannies, then it's a much
bigger deal.

If you always use a complex passphrase it will discourage people from
encrypting mail (because it becomes a hassle) which is contrary to my
own goal. But on the other hand, I fully understand that some people
actually DO need strong security for their communication, and they
should use strong passphrases, smartcards etc. I guess the best
combination is to have two keys: one for actually important stuff, and
one for mundane stuff where it doesn't matter too much if someone gets
hold of your key. Of course, if you use your key to validate your
identity then you also need to keep your key secure.

> IMHO that's something the user should care for himself, that's not
> something
> a GUI should implement. Choose a reasonable passphrase on your master
> device,
> distribute your key by USB flashdrive / email / dropbox / encrypted ANYbox
> and change the passphrase to your needs.
The UI should strive to make common use cases as simple and secure as
possible. When it comes to security, the more a user has to figure out
on her own, the less secure their solution usually is.

Bad UI:
Machine A): Go to key management. "Huh, I can only export to a file. OK,
I'll use dropbox, I usually use that to share files!" Export key to your
dropbox folder. (BAM, NSA et al. now have a copy of your weak key).
Machine B): Go to key management, import key from your dropbox folder.

Good UI:
Machine A): Go to key management. "Oh, there's an option here to export
my private key. Nice! Oh, it's telling me to pick a long passphrase, and
I don't need to use it regularly. OK, in that case I might as well make
it really long and complicated.". Send key via email. By default email
contains instructions saying that the key is protected by the password
you just picked, not the usual one.
Machine B): Open email, import key just like normally. UI recognizes
that it's a private key and asks if you want to change the password.

In the first case the user had to come up with their own (insecure)
solution to the problem, in the second case they were guided through the
process and basically didn't need to think much for themselves.
Importing a secret key is pretty rare, so asking if the user wants to
change password is not too much of an extra hassle considering the
improvement in usability and security (IMHO). You can even add a
checkbox not to show the alert, so it would be shown only once to people
who don't need it.

-- 
Stefan Parviainen

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