diff --git a/ObsoleteFiles.inc b/ObsoleteFiles.inc
index e53a91aaa24..13c9156a7de 100644
--- a/ObsoleteFiles.inc
+++ b/ObsoleteFiles.inc
@@ -144,6 +144,12 @@ OLD_FILES+=libexec/casper/grp
 OLD_FILES+=libexec/casper/pwd
 OLD_FILES+=libexec/casper/random
 OLD_FILES+=libexec/casper/sysctl
+OLD_FILES+=libexec/casper/.debug/random.debug
+OLD_FILES+=libexec/casper/.debug/dns.debug
+OLD_FILES+=libexec/casper/.debug/sysctl.debug
+OLD_FILES+=libexec/casper/.debug/pwd.debug
+OLD_FILES+=libexec/casper/.debug/grp.debug
+OLD_DIRS+=libexec/casper/.debug
 OLD_DIRS+=libexec/casper
 OLD_FILES+=usr/lib/libcapsicum.a
 OLD_FILES+=usr/lib/libcapsicum.so