On 07/18/2013 03:24 AM, Ronald Oussoren wrote:
I'm trying to understand what this means for package maintainers. If I understand you 
correctly maintainers would upload packages just like they do now, and packages are then 
automaticly signed by the "unstable" role.  Then some manual process by the 
PyPI maintainers can sign a package with a stable row. Is that correct? If it is, how is 
this supposed to scale? The contents of PyPI is currently not vetted at all, and it seems 
to me that manually vetting uploads for even the most popular packages would be a 
significant amount of work that would have to be done by what's likely a small set of 
volunteers.

I think Daniel put it best when he said that we have been focusing too much on deciding whether or not a package is malicious. As he said, it is important that any security proposal must limit what targeted attacks on the PyPI infrastructure can do.

You are right that asking people to vet through packages for inclusion into the stable role would be generally unscalable. I think the best way to think about it is that we can mostly decide a "stable" set of packages with a simple rule, and then *choose* to interfere (if necessary) with decisions on which packages go in or out of the stable role. The stable role simply has to sign this automatically computed set of "stable" packages every now and then, so that the impacts of attacks on the PyPI infrastructure are limited. Users who install the same set of stable packages will see the installation of the same set of intended packages.

Presently, I use a simple heuristic to compute a nominal set of stable packages: all files older than 3 months are considered to be "stable". There is no consideration of whether a package is malicious here; just that it has not changed long enough to be considered mature.

Also, what are you supposed to do when FooBar 2.0 is signed by the stable role 
and FooBar 2.0.1 is only signed by the unstable role, and you try to fetch 
FooBar 2.0.* (that is, 2.0 or any 2.0.x point release)?


In this case, I expect that since we have asked pip to install FooBar 2.0.*, it will first fetch the /simple/FooBar/ PyPI metadata (distinct from TUF metadata) to see what versions of the FooBar package are available. If FooBar 2.0.1 was recently added, then the latest version of the /simple/FooBar/ metadata would have been signed for the unstable role. There are two cases for the stable role:

1. The stable role has also signed for the FooBar 2.0.1 package. In this case, pip would find FooBar 2.0.1 and install it. 2. The stable role has not yet signed for the FooBar 2.0.1 package. In this case, pip would find FooBar 2.0 and install it.

Why would this happen? In this case, we have specified in the TUF metadata that if the same file (in this case, the /simple/FooBar/ HTML file) has been signed for by both the stable and unstable roles, then the client must prefer the version from the stable role.

Of course, there are questions about timeliness. Sometimes users want the latest packages, or the developers of the packages themselves may want this to be the case. For the purposes of bootstrapping PyPI with TUF, we have presently decided to simplify key management and allow for the protection of some valuable packages on PyPI (with limited timeliness trade-off) while allowing for the majority of the packages to be continuously released.

There are a few ways to ensure that the latest intended versions of the FooBar package will be installed: 1. Do not nominate FooBar into the "stable" set of packages, which should ideally be reserved --- for initial bootstrapping purposes at least --- for perhaps what the community thinks are the "canonical" packages that must initially be protected from attacks. 2. The stable role may delegate its responsibility about information on the FooBar package to the FooBar package developers themselves. 3. Explore different rules (other than just ordering roles by trust) to balance key management, timeliness and other issues without significantly sacrificing security.

We welcome your thoughts here. For the moment, we are planning to wrap up as soon as possible our experiments on how PyPI+pip perform with and without TUF with this particular scheme of stable and unstable roles.

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