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Comment by thex86 | Hacker News Reader

That's a great point. Reminds of the time I taught my friend to use PGP and sent him an encrypted email. Every single time, he would reply in plain-text, thus exposing my older conversation. When asked why, he told me it's too much of a pain to do it. So my being careful about my privacy doesn't help if other people don't play along.

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I've been experimenting with encrypting using bitcoin addresses, publishing keys with gravatar and sending encrypted messages as links as a way of trying to make all this stuff easier and more accessible. If you're interested in my proof of concept, it's http://kybernetikos.github.io/VisualSecrecy/

Linking bitcoin address to email address doesn't sound like a step forward in privacy...

Depends what you want to use it for. Anyway, you can have multiple bitcoin addresses for different purposes.

On top of that, while I wouldn't rely on this cryptographically, the relationship is one-way. Gravatar links email addresses to gravatar images, but it's not intended to link in the other direction, so the same is true for any information stored in the gravatar.

You can use my system to reply with encrypted text to a comment on a blog post without knowing the email address of the person you're replying to, only their gravatar image.

The OTR plugin for Pidgin does a better job of userfriendliness and gives more useful privacy guarantees (like plausible deniability).

FYI, last I remember, Pidgin stored your passwords in plaintext in an ASCII file on disk, unless you jumped through some hoops to integrate it with your desktop environment's keyring. They even have a article up on their site explaining why it's necessary to do this.

https://developer.pidgin.im/wiki/PlainTextPasswords well that's just great.

You can disable storing passwords. If you don’t want to have to enter a ‘master password’ when Pidgin starts up, there is no way they can store the passwords more securely than plaintext.

Get full disk encryption and be happy.

That's simply not true. For example, on Windows, they can use CryptProtectData. Mac OS has a keychain function too. Pidgin devs are being disingenuous by suggesting that accessible to current user is identical to storing plaintext on disk.

Full disk encryption and per-user encryption are good steps. But an accidental backup of Pidgin will still reveal passwords that would be safe if they bothered to use platform specific APIs for such storage.

Pidgin is predominantly developed for Linux, where they would have to support Gnome, KDE and probably at least one other mechanism. Sure, that could be done, but it is a lot of work to do that sensibly on all platforms, and, more importantly, of questionable sense: I would classify the logs of my conversation as much more relevant to a potential attacker than the mere password to my XMPP account.

All of this is true. But when the Pidgin devs state things like "there's no way" and "it's just as secure" (as they do on the wiki), that's just incorrect. An intellectually honest description would note that many platforms offer protection, but it's not standardized across Linux (I'm assuming).

The logs of the conversation can be protected in the same way, so I'm not sure what that has to do with anything. (Although you might wish to keep logs as plaintext, to facilitate backups, if you're not backing up the user's keychain info.)

The wiki explicitly says (under “Is that the final word?”):

> No. The Pidgin developers are generally open to, and would encourage integration with keyrings (KeyringSupport).

and then goes on to state that this is difficult to do, since Pidgin runs on so many different platforms, then stating again that they will happily accept such patches.

However, I find it understandable, that the devs don’t go out of their way to support use-cases they don’t feel necessary to support. On their systems, they trust the filesystem and are happy with that, if others don’t have that level of trust in their computer, that’s fine, but not necessarily their problem.

My point about the logfiles was that to store these in the keyring (rather than a key to the encrypted files) would probably annoy the keyring somewhat (at least the poorer implementations thereof), given that it is intended for use with few-byte passwords and not multi-megabyte logfiles.

The wiki does mention some info, yes. But it also makes a false comparison, noting how you can extract passwords on a system, and implying that the level of security is identical. That's 100% false, and to suggest so is being very misleading.

As far as logs, do what everyone does when you can only store a bit of material: Store your bulk encryption key there.

This is the exact reason I created this: https://privatemsg.matthew-dove.com/

Where can I grab source code?

Can such kind of reply put your secret key in the risk? For example, it gives attacker enough information to deduce the key within reasonable time?

I don't believe so. I think the parent comment was more concerned about the message itself being sent in the clear.

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