Why does OpenBSD-i386 build fail on des-586.s with “Unimplemented segment type”?
As of 0.9.7 assembler routines were overhauled for position independence of the machine code, which is essential for shared library support. For some reason OpenBSD is equipped with an out-of-date GNU assembler which finds the new code offensive. To work around the problem, configure with no-asm (and sacrifice a great deal of performance) or patch your assembler according to http://www.openssl.org/~appro/gas-1.92.3.OpenBSD.patch. For your convenience a pre-compiled replacement binary is provided at http://www.openssl.org/~appro/gas-1.92.3.static.aout.bin. Reportedly elder *BSD a.out platforms also suffer from this problem and remedy should be same. Provided binary is statically linked and should be working across wider range of *BSD branches, not just OpenBSD.