Use the -o flag to portupgrade to replace the perl5 port with a the perl5.8 port:
# portupgrade -rR -o lang/perl5.8 lang/perl5
After the upgrade (this is applicable after any Perl ports upgrade, such as 5.8.8 to 5.8.9), run the perl-after-upgrade script, first in test mode, then in fix mode:
# perl-after-upgrade
# perl-after-upgrade -f
Fix any errors highlighted by perl-after-upgrade, and reinstall any required packages. Review files left behind from the older Perl installation (typically /usr/local/lib/perl5/site_perl/5.X.Y/). After verifying that the upgraded Perl works as expected, remove +CONTENTS.bak files from subdirectories under /var/db/pkg.
See the perl-after-upgrade man page for more details.
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