I think it's Test::TCP that is broken on Windows. It relies on fork(), and I don't think that sockets and fork() play well under plain Win32. You seem to be using Cygwin, so maybe the problem lies elsewhere, but maybe the problems extend from plain Win32 to Cygwin as well.
My approach to debugging this would be to run the Test::TCP tests in isolation:
> cpanm --look Test::TCP
C:\...Test-TCP> perl Makefile.PL
C:\...Test-TCP> make test
C:\...Test-TCP> perl -Ilib t\test-that-hung-or-failed.t
... debug the test
C:\...Test-TCP> make install
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