Crypto can't be easy and safe. You need to check fingerprints (attempts to make this "friendly" with images and the like have tended to have vulnerabilities). Beyond that, what's your issue with OTR? A separate network has the advantage of not having to do the negotiation step of OTR-over-jabber/AIM/etc, but it will have bootstrapping problems (or maybe not; maybe a well-designed app that just used OTR all the time, on a new network, would be enough).
It's not that black and white. Yes, usability tends to carry with it some measure of sacrifice in security, but Skype used to have a lot more security, and was as easy to use as it is today. They're not absolutes. You can have "quite usable and very secure" and "very usable and quite secure", things none of the apps we're discussing are.
I don't have any big concerns with OTR (aside from the inability to do offline messaging,) just the implementions, mainly OTR in Adium. OTR in Pidgin appears to be decent, but hasn't received a lot of review, as far as I know, and Pidgin has its own problems/provides its own attack surface.
Skype was never meaningfully secure; the code wasn't open and you had to trust their servers to handle authentication. (And IIRC the best-guess reverse engineering of the crypto looked to be RC4, which while not outright broken is not a massively secure cipher).
I didn't say it had a satisfactory level of security, just that it was a lot more secure than it is now, and still had the same level of usability that it does today.
I think it's misleading to say "more secure". It wasn't secure and I can't think of any realistic attack scenario that it would have been secure against (but now isn't); for the NSA to intercept everyone's messages while it was more distributed would have required releasing a version update and waiting for the supernodes to pick it up, but that's not a high bar.
I think it's misleading to insinuate that security is an absolute, but, again, you're missing my point. I'm not telling anyone to use Skype. I'm saying that the added security didn't come at a cost to usability.
for the NSA to intercept everyone's messages while it was more distributed would have required releasing a version update and waiting for the supernodes to pick it up, but that's not a high bar.
I would say that your bar is very high, then. This would defeat nearly everything that exists and is in use today.
Also, there's probably no one in the world that can actually defend themselves against the NSA if the NSA is determined to know what they, specifically, are doing.
I'm not telling anyone to use Skype. I'm saying that the added security didn't come at a cost to usability.
What added security? I didn't say it's impossible to be easy and as safe as older versions of skype (which is to say, not very). I said it's impossible to be easy and safe. (In particular, you need some kind of key fingerprint checking, and no-one's found an effective, user-friendly way to do that).
I would say that your bar is very high, then. This would defeat nearly everything that exists and is in use today.
It wouldn't defeat GPG, or OTR-based systems used in reasonably popular open-source clients.
Also, there's probably no one in the world that can actually defend themselves against the NSA if the NSA is determined to know what they, specifically, are doing.
Sure. But let's look at a realistic threat model, and at what's actually happened: the NSA did intercept all communications channels run by individual providers, including skype. The NSA was prepared to demand these providers deploy new backdoors into software they distributed that didn't currently have them, as we saw with lavabit and RSA, and when lavabit refused they were shut down. The NSA were not terribly effective at compromising open, respected standards (they did succeed in getting a broken algorithm standardized, but the main reason this wasn't noticed is that hardly anyone was using it, and even then questions were being raised in the crypto community), and did not compromise GPG or similar open-source projects. Nor did they tap users of those systems indirectly by compromising their email clients or similar. Observe that Snowden, with inside knowledge, chose to use PGP to communicate with journalists, and this did in fact provide sufficient security.
It wouldn't defeat GPG, or OTR-based systems used in reasonably popular open-source clients.
Until you consider where GPG and OTR are used, e.g. Enigmail or Pidgin, addons or clients which both autoupdate or ask to be updated.
There are very, very, very few pieces of software that either don't need to be updated, or can't trivially be backdoored by the vendor itself through updates.
You keep going back to "Skype didn't have security"--and I can't tell if you're trolling, or what--but you can't seriously harp on it for auto-updating. So does Chrome, and it's lauded for auto-updates (the downside of not updating is obviously that security issues aren't fixed, arguably a much bigger risk than the vendor backdooring the software in later updates.)
Until you consider where GPG and OTR are used, e.g. Enigmail or Pidgin, addons or clients which both autoupdate or ask to be updated.
I can't speak to those; I use KMail and Kopete, neither of which auto-updates. My OS does ask to update those packages, but it will only do so with my explicit intervention, there's a code signing process in place (and any bad updates would be traceable to individuals rather than an institution), and the people who run it are based outside the US.
Comments
Crypto can't be easy and safe. You need to check fingerprints (attempts to make this "friendly" with images and the like have tended to have vulnerabilities). Beyond that, what's your issue with OTR? A separate network has the advantage of not having to do the negotiation step of OTR-over-jabber/AIM/etc, but it will have bootstrapping problems (or maybe not; maybe a well-designed app that just used OTR all the time, on a new network, would be enough).
It's not that black and white. Yes, usability tends to carry with it some measure of sacrifice in security, but Skype used to have a lot more security, and was as easy to use as it is today. They're not absolutes. You can have "quite usable and very secure" and "very usable and quite secure", things none of the apps we're discussing are.
I don't have any big concerns with OTR (aside from the inability to do offline messaging,) just the implementions, mainly OTR in Adium. OTR in Pidgin appears to be decent, but hasn't received a lot of review, as far as I know, and Pidgin has its own problems/provides its own attack surface.
Skype was never meaningfully secure; the code wasn't open and you had to trust their servers to handle authentication. (And IIRC the best-guess reverse engineering of the crypto looked to be RC4, which while not outright broken is not a massively secure cipher).
I didn't say it had a satisfactory level of security, just that it was a lot more secure than it is now, and still had the same level of usability that it does today.
I think it's misleading to say "more secure". It wasn't secure and I can't think of any realistic attack scenario that it would have been secure against (but now isn't); for the NSA to intercept everyone's messages while it was more distributed would have required releasing a version update and waiting for the supernodes to pick it up, but that's not a high bar.
I think it's misleading to insinuate that security is an absolute, but, again, you're missing my point. I'm not telling anyone to use Skype. I'm saying that the added security didn't come at a cost to usability.
I would say that your bar is very high, then. This would defeat nearly everything that exists and is in use today.
Also, there's probably no one in the world that can actually defend themselves against the NSA if the NSA is determined to know what they, specifically, are doing.
What added security? I didn't say it's impossible to be easy and as safe as older versions of skype (which is to say, not very). I said it's impossible to be easy and safe. (In particular, you need some kind of key fingerprint checking, and no-one's found an effective, user-friendly way to do that).
It wouldn't defeat GPG, or OTR-based systems used in reasonably popular open-source clients.
Sure. But let's look at a realistic threat model, and at what's actually happened: the NSA did intercept all communications channels run by individual providers, including skype. The NSA was prepared to demand these providers deploy new backdoors into software they distributed that didn't currently have them, as we saw with lavabit and RSA, and when lavabit refused they were shut down. The NSA were not terribly effective at compromising open, respected standards (they did succeed in getting a broken algorithm standardized, but the main reason this wasn't noticed is that hardly anyone was using it, and even then questions were being raised in the crypto community), and did not compromise GPG or similar open-source projects. Nor did they tap users of those systems indirectly by compromising their email clients or similar. Observe that Snowden, with inside knowledge, chose to use PGP to communicate with journalists, and this did in fact provide sufficient security.
Meaningful security is possible. Skype isn't it.
Until you consider where GPG and OTR are used, e.g. Enigmail or Pidgin, addons or clients which both autoupdate or ask to be updated.
There are very, very, very few pieces of software that either don't need to be updated, or can't trivially be backdoored by the vendor itself through updates.
You keep going back to "Skype didn't have security"--and I can't tell if you're trolling, or what--but you can't seriously harp on it for auto-updating. So does Chrome, and it's lauded for auto-updates (the downside of not updating is obviously that security issues aren't fixed, arguably a much bigger risk than the vendor backdooring the software in later updates.)
I can't speak to those; I use KMail and Kopete, neither of which auto-updates. My OS does ask to update those packages, but it will only do so with my explicit intervention, there's a code signing process in place (and any bad updates would be traceable to individuals rather than an institution), and the people who run it are based outside the US.