On Dec 31, 2014, at 2:05 PM, Paul Moore email@example.com wrote:
On 31 December 2014 at 18:42, Donald Stufft firstname.lastname@example.org wrote:
Just to speak to these two points. The purpose behind having a developer sign some files is that you can verify that those files were signed by the person holding the private key belonging to that developer.
Thanks for the explanation.
Ideally you would not use the same password as you use for logging into PyPI because you send that password to PyPI anytime you login which would mean that PyPI would more or less know your private key.
My problem with this logic is that there's another attack vector that this ignores - what if someone gets access to my PC, which has all of these passwords in a "saved password" store that I use because it's a pain to manage so many passwords (I don't, but you get the point ;-))? I work in a number of secure environments where multiple complex passwords are mandated - and typically password management becomes sufficiently hard that people start to use shortcuts, defeating the object of the whole exercise (heck, end users probably just use "Password01" everywhere, "because it's too hard to remember all those passwords"...)
That's not to say that bad security practices justify anything, but on the other hand human factors do imply that it's not automatically guaranteed that two passwords are more secure than one. Single sign-on is a goal for a lot of people for a reason...
Basically if your private key, whether it’s a file or it’s a password gets compromised than the person who compromises your private key can masquerade as you without anyone being able to detect the difference. At that point the private key will need to be revoked (as in, programmatically announced as compromised and no longer valid).
There’s basically no way to have a signing solution that doesn’t involve some secret bit of data that is known only to you and is never sent to PyPI. As with most things on PyPI we cannot actually mandate that a user practices good security with their private key. They could, for instance, post it on Twitter and there isn’t much that we can do about it. The only way to avoid that is to more or less give up on the idea of surviving a compromise of the PyPI infrastructure. That isn’t itself a *wrong* answer, since signing does impose additional cost to the author and it’s not entirely clear that the cost is worth it.
One of the benefits of having the author sign is that you get a chain of what is called an offline key. Essentially all trust comes from pip trusting a set of “root” keys which are not stored on a server in the PyPI infrastructure and are instead stored “offline” in some fashion such as on a USB drive sitting in a safe deposit box, or in an HSM (for the uninitiated, a HSM is a hardware device that stores keys but does not allow you to get the key itself back out. You can use the key by asking the HSM to do operations with it but you can’t get the key back out. Some HSMs even include things like an acid pack inside of them where attempting to physically open the HSM will break the acid pack and destroy the internal memory that holds the key). Then from that root key(s) you can go from key to key in a chain until you get to the author key, and every key in that chain is not stored “online”.
This chain of offline keys means that if someone takes over the machines running PyPI they can’t trick people into installing something because the keys that are required to do that don’t exist on PyPI.
Like most things in security however, there is no singular right answer and everything is a tradeoff. In this particular case the tradeoff we need to make is between the ability to survive a compromise of the PyPI machines themselves and the UX for end users. For example, if we make signing mandatory and the UX is bad then we're going to hamper the ability for authors to publish new downloads. If that UX is bad enough we can get into a situation where authors choose not to release things as often as they would otherwise prefer to because of the pain associated with releasing. There are also concerns that by making signing mandatory that it's going to have people who have no interest or desire in properly securing a private key being forced to make one and they might just use the same password as they use for PyPI or something like "hunter1" or whatever. In that case for those people and the users of their projects we've not added much additional security but we've increased complexity and the chances of something breaking. If we make signing optional however, then the benefit might not be worth exposing signing to end users. If, for example, an end users downloads and installs 100 different files from PyPI and 99 of them the author opted in to signing them and one of them the author didn't then a compromise of PyPI can compromise that end user through just that one project.
I don't believe there is any downside to moving away from relying solely on TLS and using a TUF based scheme where PyPI itself holds the signing keys. That's a net win since you're changing having the PyPI infrastructure manage TLS keys for having the PyPI infrastructure manage TUF keys with the added benefit that TUF "transfers" in ways that TLS simply can't (such as through the CDN or through mirrors or what have you).
There *may* be enough downside to having authors sign that it doesn't make sense to expose that. Part of the discussion around PEP 480 should be hammering out what the UX looks like for the authors, deciding if that UX is good enough to make it mandatory or to make it strongly encouraged through pip warnings and PyPI warnings, and ultimately deciding if the tradeoff of the additional burden on authors is worth it. If it's not worth it to the community as a whole then we shouldn't accept PEP 480 and should instead focus on ensuring that we reduce the ability to compromise PyPI itself (which is something we should do anyways of course). In this regard having the opinion from someone who isn't an expert is *extremely* helpful because someone like me already knows how to manage their keys and already does it so for people like me the answer for if having authors needing to manage some secret bit of data is asking too much is an easy answer. No it's not too much to ask me to do that because I'm already doing it (and a lot of developers are via their SSH private keys for instance).
(How's that for a tl;dr?)
--- Donald Stufft PGP: 7C6B 7C5D 5E2B 6356 A926 F04F 6E3C BCE9 3372 DCFA