It is well known issue with build on Windows: It requires ActivePerl to correctly create configuration. Every other Perl implementation fails to execute correctly. The reason it fails outlined in this report: https://github.com/openssl/openssl/issues/174 Although it is stated that only cloned code exhibits this behavior I believe it also happens when Git or Strawberry Perl is being used for build of official releases.
As suggested in the comments adding $/= "\r\n"; line to Perl script fixes this issue for every other Perl implementation. I've successfully built openssl with Perl distributed with Git as well as Strawberry Perl.
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