Ok, I have still not been able to reproduce this.
We have already established that the perl you use is the mingw one,
haven't we? (if we haven't, that really needs to be checked.
Matching perl and all that)
A test to figure out is this:
perl util/mkdef.pl 32 crypto debug 2> mkdef-debug.txt
Ok, progress (sort of)! It turns out I was indeed using the wrong
version of perl -- I was using the perl that was installed as part of
the msys2 base-devel group, not the mingw-w64--perl package,
which is a whole separate thing.
However, having installed the mingw-w64 version of perl, the
> Ok, I have still not been able to reproduce this.
Neither have I!
I've just downloaded OpenSSL 1.1.0f and built it from source.
This is my configuration:
Microsoft Windows [Version 10.0.15063]
This is perl 5, version 24, subversion 1 (v5.24.1)
GCC v6.3.0 (64-bit)
./config mingw64