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A thorough PGP tutorial

futureboy.us

31–40 of 115 posts

Re: A thorough PGP tutorial

#31
post #24
post #20

Earlier quoted context omitted.

I hear this, but I have absolutely zero idea how to get s/mime working and I'm faintly aware it might involve having to buy a digital certificate off someone (and doesn't that mean that someone could decrypt my email anyway? if they're the ones who generate the certificate?) What I'm trying to say here is: I'm a bit of a geek, and if I don't understand how it works, there's no way e.g. my parents are. If s/mime is th…

No, you generate your own, then have the public key signed by a CA having proven your identity to some greater or lesser degree, depending on the level of certification - but generating your own and having it signed is not a straightforward process in my (limited) experience.

The problem with that method is the recipient of your mail is still relying on that CA to validate your public key. The CA could (willingly or under duress) sign some other public key and claim it's yours, then use that key to impersonate you, and even trick recipients into using that public key to encrypt emails intended for you. That would form the basis of a man-in-the-middle attack. It's unlikely to work if you've already been communicating using the real public key (depending on how the software handles new keys), but for new recipients in particular, it's possible.

Re: A thorough PGP tutorial

#32
post #18
post #14

There have been several calls in recent weeks for a nice UX wrapping GPG. I'm thinking of what Cryptocat aims to be, but with a sound implementation resting on GPG. The crypto community seems supportive of this idea. I'm not saying I'd be the one to implement this, but at the vert least, I'd like to start collecting ideas. Maybe I or someone else could realize them eventually. So let's talk. Please post your thoughts…

use S/MIME, leave gpg for special cases. S/MIME works everywhere (Outlook, Mail.app, iOS, Thunderbird, BlackBerry, Windows Phone, Lotus, ... ) out of the box. No plugins required.

Do you mean we should build a good UX around S/MIME? It seems clear to me that none currently exists.

I'd be curious to hear from security specialists about S/MIME. How thoroughly studied is it? How are the libraries? I have hardly ever heard it discussed, so I'm a little hesitant at the moment.

Re: A thorough PGP tutorial

#33
post #31
post #24

Earlier quoted context omitted.

No, you generate your own, then have the public key signed by a CA having proven your identity to some greater or lesser degree, depending on the level of certification - but generating your own and having it signed is not a straightforward process in my (limited) experience.

The problem with that method is the recipient of your mail is still relying on that CA to validate your public key. The CA could (willingly or under duress) sign some other public key and claim it's yours, then use that key to impersonate you, and even trick recipients into using that public key to encrypt emails intended for you. That would form the basis of a man-in-the-middle attack. It's unlikely to work if you'v…

that's possible with PGP, too, if you don't verificate key in person. E.g. "hey Alice, I lost my passphrase, please use the attached key or ID xxxx on one of the keyservers"

It's even easier to do, because you don't have to trick a CA in creating a duplicate key.

Re: A thorough PGP tutorial

#34
post #14

There have been several calls in recent weeks for a nice UX wrapping GPG. I'm thinking of what Cryptocat aims to be, but with a sound implementation resting on GPG. The crypto community seems supportive of this idea. I'm not saying I'd be the one to implement this, but at the vert least, I'd like to start collecting ideas. Maybe I or someone else could realize them eventually. So let's talk. Please post your thoughts…

iPGMail http://ipgmail.com The website is pretty helpful.

Yes, that's a step in the right direction. (In terms of UX. I won't make any claims either way about its security.) In any case, I'd definitely want a solution that works on the desktop. I don't know if iPGP integrates with keyservers, but that would also be an important feature.

Re: A thorough PGP tutorial

#35
post #14

There have been several calls in recent weeks for a nice UX wrapping GPG. I'm thinking of what Cryptocat aims to be, but with a sound implementation resting on GPG. The crypto community seems supportive of this idea. I'm not saying I'd be the one to implement this, but at the vert least, I'd like to start collecting ideas. Maybe I or someone else could realize them eventually. So let's talk. Please post your thoughts…

I'd call out something I mentioned in my other comment in this thread: Enigmail + Thunderbird makes it pretty easy to get PGP up and running. Make an elegant doc on configuring that, put up a refreshing landing page, and you're golden.

Re: A thorough PGP tutorial

#36
post #32
post #18

Earlier quoted context omitted.

use S/MIME, leave gpg for special cases. S/MIME works everywhere (Outlook, Mail.app, iOS, Thunderbird, BlackBerry, Windows Phone, Lotus, ... ) out of the box. No plugins required.

Do you mean we should build a good UX around S/MIME? It seems clear to me that none currently exists. I'd be curious to hear from security specialists about S/MIME. How thoroughly studied is it? How are the libraries? I have hardly ever heard it discussed, so I'm a little hesitant at the moment.

It's already build in e.g. Mail.app.

We need no software. We need public awareness, tutorials and probably some easy to use CA.

I bet the adoption rate of S/MIME is way beyond gpg if you check corporations and large enterprises.

for example: Germany

https://gist.github.com/rmoriz/5945400

Re: A thorough PGP tutorial

#37
post #14

There have been several calls in recent weeks for a nice UX wrapping GPG. I'm thinking of what Cryptocat aims to be, but with a sound implementation resting on GPG. The crypto community seems supportive of this idea. I'm not saying I'd be the one to implement this, but at the vert least, I'd like to start collecting ideas. Maybe I or someone else could realize them eventually. So let's talk. Please post your thoughts…

I think a plugin that whould do the following whould be great allready: "Paste and crypt" paste text into field or mark it. hit encrypt. pop/menu/whatever lets you choose or import public keys. "paste and decrypt" basically the same funtionality backwards

Do you mean a browser plugin? Probably the biggest issue currently is that browser plugins tend to be written in JS. See this for why it's a problem:

http://www.matasano.com/articles/javascript-cryptography/

If we someday have an ecosystem of C browser extensions, in-browser crypto may be much more promising. Or not. I suppose there could be other problems besides the language.

Re: A thorough PGP tutorial

#38
post #25
post #14

There have been several calls in recent weeks for a nice UX wrapping GPG. I'm thinking of what Cryptocat aims to be, but with a sound implementation resting on GPG. The crypto community seems supportive of this idea. I'm not saying I'd be the one to implement this, but at the vert least, I'd like to start collecting ideas. Maybe I or someone else could realize them eventually. So let's talk. Please post your thoughts…

A simple and secure means to copy your private key between devices would be high on my list.

Yes, very good point. I'd probably be in favor of having two ways of doing it:

* Some kind of "sync" for people who hate dealing with files.

* Copying a single file by whatever means you see fit, such as a USB stick. Many people, such as myself, prefer the simplicity and transparency of a good old file.

Each of these has potential security pitfalls. Those would have to be thought out.

Re: A thorough PGP tutorial

#39
post #36
post #32

Earlier quoted context omitted.

Do you mean we should build a good UX around S/MIME? It seems clear to me that none currently exists. I'd be curious to hear from security specialists about S/MIME. How thoroughly studied is it? How are the libraries? I have hardly ever heard it discussed, so I'm a little hesitant at the moment.

It's already build in e.g. Mail.app. We need no software. We need public awareness, tutorials and probably some easy to use CA. I bet the adoption rate of S/MIME is way beyond gpg if you check corporations and large enterprises. for example: Germany https://gist.github.com/rmoriz/5945400

I've thought some more about S/MIME, and right now my biggest concern is the CAs. I don't like having that central point of trust/failure.

Do you know if S/MIME can work on a distributed model?

Also, what are the advantages of S/MIME over PGP? I hear what you're saying about enterprise adoption, but I'm more concerned with the thoroughness of peer review than usage rates.

Re: A thorough PGP tutorial

#40
post #31
post #24

Earlier quoted context omitted.

No, you generate your own, then have the public key signed by a CA having proven your identity to some greater or lesser degree, depending on the level of certification - but generating your own and having it signed is not a straightforward process in my (limited) experience.

The problem with that method is the recipient of your mail is still relying on that CA to validate your public key. The CA could (willingly or under duress) sign some other public key and claim it's yours, then use that key to impersonate you, and even trick recipients into using that public key to encrypt emails intended for you. That would form the basis of a man-in-the-middle attack. It's unlikely to work if you'v…

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