in reply to Date::Calc Install Fails

Well, the installer did, actually, try to tell you:

Failed 3/51 test programs. 60/3381 subtests failed.
dmake.exe: Error code 255, while making 'test_dynamic'

... but it’s not too obvious, sometimes, and it’s not always 100% reliable.   Sometimes, I find, you must download the actual package installation and/or test scripts and l-o-o-k at them.   Also, to guess that the underlying implementation might involve XS (that is to say, “C” code that is being called-upon by Perl to do the actual work ...), and especially if an interface to some .DLL or .so library might be involved.   If that is the case, then the CPAN module, and therefore its installation and its testing scripts, will be doing a lot of hand-waving ... and a lot of very- environment-specific things might be going wrong, which might be very particular to your environment.

Another useful thing to check out at cpan.org are the open-bug reports and the “CPANTS = CPAN Testing Service” results.   Most CPAN packages are actually automatically-tested on a variety of production environments, and one of them is quite likely to resemble yours.   It might be a bit hard-to-find the necessary hyperlinks on the CPAN site, but they are there.   If “environment-specific things” might go-wrong, there’s a very good chance that The Pants™ knows about it already.