On Oct 26, 2015, at 5:48 AM, Andrey Repin <anrdae...@yandex.ru> wrote:
> 
> MD5 hash proven weak

That’s a bit strong.  It’s better to say that MD5 has weak collision resistance 
properties, which in this context means it is possible to generate a Cygwin 
package with arbitrary contents that produces the same hash as the legitimate 
package, in a computationally useful time frame.

But, that is not the value MD5 is providing to setup.exe.  If you are 
downloading a package from bad-actor.com, you are also downloading setup.ini 
from there, so they can rewrite the hashes.  Only if you take the extra step to 
get your setup.ini from a different site can you cross-check the hashes.

Even then, all it proves is that the file you downloaded is the one the server 
claims to be providing.  It doesn’t prove provenance, which is what people 
really seem to want, when they go hand-checking hashes.

One way to solve that would be for cygwin.com could run a special-purpose CA, 
and for the process that moves uploaded packages into the distribution 
directory to sign them using the CA’s private key.  Then setup.exe can 
cryptographically prove to itself that it is installing legitimate packages.
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