Currently Cygwin-ports has problems countering man-in-the-middle (MITM) attacks 
when it installs/updates software.
The good news is that this is easy to fix.

Problem 1: The GPG key isn't acquired in some authenticated way.
Currently, users get the key by viewing http://cygwinports.org/
and downloading the GPG key using http.  That's vulnerable to MITM.

The obvious solution, now used by Cygwin itself, is to switch cygwinports.org
to use https.  ideally it'd be https-only, using HSTS, like Cygwin itself.

Problem 2: Currently MD5 is used as the hash function in the setup.ini files.
The current Cygwin installer now supports SHA-512, and Cygwin intends to
switch to SHA-512 soon in its setup.ini file.  I recommend the same things
happen in cygwin-ports.

Thanks!

--- David A. Wheeler


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