Working with darwinports, it looks like building OpenSSL on a UFS volume (mounted as NFS) and installing from there to a local HFS+ volume has problems. For some reason, the port won’t install due to some filename case issues if the source files are on an NFS volume. If I do it all locally, it works fine.
I don’t get it. I would have suspected the target filesystem to be the issue, rather than the source one.