Currently 'pkg_rolling-replace' gives an error while upgrading 'bootstrap-mk-files' tnn@ answered your real question, but I'd like to point out that pkg_rolling-replace does "make replace" in the right order. If the order is right, but the make replace fails, then the problem is *not* a pkg_rolling-replace problem, but a problem with the underlying make replace mechanism. In this case, and probably for pkg_install, things work better with DESTDIR, because without it there is a time when the bootstrap-mk-files are missing but needed. I used to work around this by rm -rf /var/db/pkg/bootstrap-mk-files* and then just 'make package', since I didn't care about dependencies being recorded and overwriting was ok. That was a kludge, though and the resulting "pkg_add -u" is better.
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