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Re:Malicious software libraries found in PyPI posing as well... by donaldstufft on Friday September 15, 2017 @04:08PM (#15260340)
Package signing doesn't achieve anything without a trust model behind it, which is exactly what that post states. Too many people go "we need to add some crypto to this thing!" without developing a threat model and that ends up making the crypto pointless wankery to act as a security blanket without actually solving any problems.

Maven Central, to my knowledge, does not have typo squatting problems because Sonatype has a manual review process for all new projects. It has absolutely nothing to do with the fact that they allow projects to upload PGP signatures and it could not have anything to do with that, because PGP does not provide any mechanism to prevent that.

For example, there may be `urllib3` which is a valid project that must be signed by key X. We'll ignore how a tool like pip would find out that key X is the right key (although this is actually the most important part of a package signing solution) and just grant that we've solved that problem. Someone then comes and registers another project, `urlib3` which must be signed by key Y. The attack that is being described here is that a user would erroneously say ``pip install urlib3`` when they meant to type ``pip install urllib3`` and pip would then fetch that and download the package and install it. I think it is pretty obvious that signing doesn't help here, because pip doesn't know that the user really wanted urllib3 and not urlib3, so it can only determine that urlib3 is supposed to be signed by key Y (which of course, the hypothetical malicious person controlling urlib3 would have), fetch the package and verify it's signature.

There is only one tried and true method for preventing across the board this kind of human introduced error collision (aka typo squatting), and that is manual review of all new projects. The problem with manual review then becomes one scale. There are as of this time of writing 117,226 unique projects on PyPI with an average growth of around 100 new projects a day. In addition there are zero full time developers or operations or support people working on PyPI. There is one part time paid person (me), plus my unpaid time, plus one other part time unpaid developer/ops person who do the vast bulk of the work. There is simply not enough available bandwidth to process 100 new projects every day and to validate them for typo squatting/confusion possibilities.

Beyond that, there are a number of possible heuristic based approaches that can try to reduce the chance of this from happening such as using levinstein distance, unicode confusables, attempting develop "reputation", etc. Most of these are either so broad as to catch a lot of projects which are not typo squatting but are real, actual different things or are so narrow as to be trivially defeated. That's not to say they aren't worthwhile or there isn't an idea that would make sense but focusing on that has not been a priority for a largely volunteer based organization because there are lower hanging fruit that are more impactful , because at the end of the day without a manual review system individual end users are still ultimately responsible for ensuring they're asking for the correct thing (and even beyond that, they're responsible for ensuring that the thing they're asking be installed is something that satisfies their own security constraints).

Security is achieved by layering multiple secure systems on top of each other, not by randomly rubbing crypto on things because it makes you feel good to have crypto involved.

Re:Malicious software libraries found in PyPI posing as well... by danjoc on Friday September 15, 2017 @04:33PM (#15260545)
>For example, there may be `urllib3` which is a valid project that must be signed by key X. Someone then comes and registers another project, `urlib3` which must be signed by key Y.

Key X is on the company approved key list, key y is not. Your argument just fell apart.

>The problem with manual review then becomes one scale. There are as of this time of writing 117,226 unique projects on PyPI with an average growth of around 100 new projects a day.

You're not dealing with projects. You're dealing with keys. It's not one key per project. It's one key per contributor. This has the added bonus that if a contributor goes rogue, you can revoke the one key and all the suspect projects are are invalidated at once.

>There is one part time paid person (me), plus my unpaid time, plus one other part time unpaid developer/ops person who do the vast bulk of the work.

Sonatype has turned this into a rather nice business. It's not a volunteer project for them. You expect me to believe it's impossible despite solid examples to the contrary?

>at the end of the day without a manual review system individual end users are still ultimately responsible for ensuring they're asking for the correct thing

Blaming the victims.

>Security is achieved by layering multiple secure systems on top of each other, not by randomly rubbing crypto on things because it makes you feel good to have crypto involved.

It's also not achieved by doing absolutely nothing at all.

Re:Malicious software libraries found in PyPI posing as well... by geofft on Friday September 15, 2017 @04:43PM (#15260618)
> You're not dealing with projects. You're dealing with keys. It's not one key per project. It's one key per contributor.

My rough guess is that for the Python community, these are roughly proportional; there are a lot of different people maintaining approximately one library each, not a small number of people (or companies) maintaining large parts of the ecosystem. There's nothing directly like org.apache for Python.

Re:Malicious software libraries found in PyPI posing as well... by danjoc on Friday September 15, 2017 @04:47PM (#15260647)
And yet in every typo squatting case, there's multiple projects leading back to a single contributor. It's almost like noticing a little known nobody sneaking to the front of the Pareto distribution would be a huge red flag.
Re:Malicious software libraries found in PyPI posing as well... by geofft on Friday September 15, 2017 @04:55PM (#15260694)
By "every typo squatting case" do you just mean researchers demonstrating the viability of the attack against various systems? A system that successfully defends against researchers but not against actual genuine attackers would be worse than useless. If I actually wanted to pull off an attack without anyone noticing for as long as possible, I'd just target a single package whose maintainer is on vacation.

I think the only way your key-signing mechanism would actually solve the problem is if we made it actively hard for new developers to upload projects to PyPI without a long vetting process. Some projects work this way (Debian, notably; I've had upload rights for a few Debian packages for years and still don't feel ready to apply for full access), but I think it's a poor match for PyPI's actual goal.

Re:Malicious software libraries found in PyPI posing as well... by danjoc on Friday September 15, 2017 @05:08PM (#15260789)
Your arguments and exaggerated claims are silly. I can point to Maven Central all day long. They're doing it right. They don't have these problems.

You know who does this sort of thing? Politicians. They can't just look at a working system, single payer for instance, and copy it. No, they have to make silly arguments about why it will never work, despite a concrete, working example, right in front of their own eyes.

Re:Malicious software libraries found in PyPI posing as well... by takluyver on Friday September 15, 2017 @05:43PM (#15261019)
Donald already pointed out that the key difference in Maven Central is a manual review process, not package signing.

If Python introduced manual review of new packages, it would either need a massive amount of resources that no-one is offering to provide, or it would immediately be a huge bottleneck on people making new packages, which the community doesn't want to do.

Re:Malicious software libraries found in PyPI posing as well... by danjoc on Friday September 15, 2017 @07:02PM (#15261573)
>the key difference in Maven Central is a manual review process

Lipstick on the pig, still covered in mud.

The key difference is the regular occurrence of malware finding its way into PyPi and NPM due to the lack of multilayered security on those repos.

You guys keep trying to prop up the straw man that ONLY package signing is needed. It's not. It's a start. Nobody is making that argument but you. You not only repeatedly beat that dead horse, but you carry it to the illogical extreme that package signing is somehow harmful. Not only do you see no value in that layer of security, but you actively resist any talk or attempts at implementing it.

Meanwhile, your repo is infested with hackers and malware. Big surprise.

Re:Malicious software libraries found in PyPI posing as well... by xapata on Saturday September 16, 2017 @01:55PM (#15265717)
Hyperbole and insults. Now you're just trolling. If I see a cockroach in the kitchen, I kill it and spray. I don't rip out the walls or move house.
Re:Malicious software libraries found in PyPI posing as well... by takluyver on Friday September 15, 2017 @05:10PM (#15260801)
That sounds like you're relying on blacklisting the 'bad guy' key that's uploading all the malicious packages. Any half-way competent bad guy will generate a new key for each package (or try to steal keys with some good reputation), so it won't work.
Re:Malicious software libraries found in PyPI posing as well... by zzzeek on Friday September 15, 2017 @04:48PM (#15260651)
> You're not dealing with projects. You're dealing with keys. It's not one key per project. It's one key per contributor. This has the added bonus that if a contributor goes rogue, you can revoke the one key and all the suspect projects are are invalidated at once.

you cannot locate said rogue contributor without regularly manually reviewing 117,226 packages.

Re:Malicious software libraries found in PyPI posing as well... by danjoc on Friday September 15, 2017 @04:53PM (#15260680)
>you cannot locate said rogue contributor without regularly manually reviewing 117,226 packages.

Herd immunity. Someone is out there reviewing it. Most users won't need to lift a finger beyond verifying signatures.

Re:Malicious software libraries found in PyPI posing as well... by donaldstufft on Friday September 15, 2017 @05:06PM (#15260779)
> Herd immunity. Someone is out there reviewing it.

More likely everyone assumes someone else is reviewing it, and nobody actually does.

Re:Malicious software libraries found in PyPI posing as well... by danjoc on Saturday September 16, 2017 @07:31PM (#15267329)
We definitely do where I work. I'm really, really surprised to hear they do not where you work. A multibillion dollar company like Amazon, who runs half the internet with AWS, does not verify dependencies? Wow. That's breathtaking.
Re:Malicious software libraries found in PyPI posing as well... by zzzeek on Friday September 15, 2017 @08:05PM (#15261874)
If 100k packages are already security audited by the community.. Then what's the issue? They send them to dstufft, he takes them down (which of course does not actually happen because nobody is auditing most packages). As mentioned elsewhere, most contributors to pypi have only one package so the notion of "find one rogue package == dozens of untrustworthy packages removed in one swoop" doesn't really exist (esp because a rogue agent would be making one account / key per package just to avoid this kind of detection!)
Re:Malicious software libraries found in PyPI posing as well... by donaldstufft on Friday September 15, 2017 @05:02PM (#15260758)
> Key X is on the company approved key list, key y is not. Your argument just fell apart.

A minuscule amount of people are going to bother to do something like approve keys. Security for the minority can already be achieved by those companies mandating their developers use DevPI and mirroring trusted projects from PyPI to DevPI (or similar system).

Complicating the system further for something that, for practical purposes, does not improve the security of the vast bulk of people is not a trade off we're willing to make. Package signing will come to PyPI, likely in the form of TUF which is strictly superior to the trust model provided by PGP for package signing. It hasn't done so because nobody has had the time to do it yet.

What you seem to be missing about my statement both in blog post and here is not that package signing is not worthwhile, but that a lot of people like yourself seem to think that all you need to do is add signatures to a system and suddenly poof it's secure! That view point is common among inexperienced developers or people who don't commonly think too hard about how secure systems are designed/made.

The reality of the situation that adding signatures is painfully easy, but that without a coherent trust model backing those signatures you've achieved nothing but adding more complexity. Determining a trust model (particularly one that works for the majority) is the hard part, and you can't just wave your hand and wish it better.

> Sonatype has turned this into a rather nice business. It's not a volunteer project for them. You expect me to believe it's impossible despite solid examples to the contrary?

Is it impossible to turn PyPI into a business? I don't suspect it is no. However I don't want to do that because my personal risk tolerance doesn't have room for giving up a stable job with health benefits for something that may or may not fail. Others are free to try that if they want of course, but given the lack of people stepping forward to do that, it doesn't seem like anyone else is interested either.

> Blaming the victims.

Stating reality. PyPI is not a curated repository and the end users is responsible for their own security while using it. If they wish to outsource that responsibility there are a number of Linux distributions that are happy to do that for them as well as companies like Enthought and Continuum Analytics who provide curated repositories.

> It's also not achieved by doing absolutely nothing at all.

Good thing we're not doing nothing at all then. Luckily for the Python community we have actual experts and not arm chair cryptographers who fail to understand even the basic fundamentals of developing secure software.

Re:Malicious software libraries found in PyPI posing as well... by danjoc on Friday September 15, 2017 @05:19PM (#15260859)
>Complicating the system further for something that, for practical purposes, does not improve the security of the vast bulk of people is not a trade off we're willing to make.

This is the weakest argument. Are Python devs somehow dumber than Java devs? Are they dumber than Android devs? Are they dumber than iOS devs? Everyone knows how to sign a dependency/app/project except python devs? I don't believe that. I honestly think that's the most insulting aspect of this argument.

The rest of this post seems to have turned to hand waving and personal attacks, so I won't bother responding to that. I'm just glad I got to share this perspective with you. Once you cool down, I hope you look harder at the problem. All I care about is improved security. I'm not here for the imaginary internet points.

Re:Malicious software libraries found in PyPI posing as well... by donaldstufft on Friday September 15, 2017 @05:33PM (#15260946)
> This is the weakest argument. Are Python devs somehow dumber than Java devs? Are they dumber than Android devs? Are they dumber than iOS devs? Everyone knows how to sign a dependency/app/project except python devs? I don't believe that. I honestly think that's the most insulting aspect of this argument.

Nope, I think they're perfectly capable of signing things. I also think it's silly to ask them to do that when the proposed system hasn't been designed to provide any benefit. Properly designing that system is hard, and 99% of people who go "just use PGP!" or "just use X" have spent exactly zero amount of time doing that. Particularly when the proposed solution doesn't actually solve the problem at hand (though it does solve other problems if it's correctly designed).

Ultimately your "suggestions" are nothing new, they're the same generic, cargo culting, suggestions that folks who haven't looked really hard at the problem tend to make.