Index: usr.sbin/freebsd-update/freebsd-update.sh
===================================================================
--- usr.sbin/freebsd-update/freebsd-update.sh
+++ usr.sbin/freebsd-update/freebsd-update.sh
@@ -2907,12 +2907,16 @@
 	sort -k 1,1 -t '|' $1 |
 	    tr '|' ' ' |
 	    while read FPATH TYPE OWNER GROUP PERM FLAGS HASH LINK; do
-		# A file may change to a directory on upgrade (PR273661).
-		# If that happens rm the file first so that install can create
-		# the directory in its place.
+		# A file may change to a directory on upgrade (PR273661) or
+		# vice-versa.  If that happens rm the file or rm -rf the
+		# directory first so that install can create the directory or
+		# file in its place.
 		if [ -e "${BASEDIR}/${FPATH}" ]; then
 			if [ ${TYPE} = d ] && ! [ -d "${BASEDIR}/${FPATH}" ]; then
 				rm -f ${BASEDIR}/${FPATH}
+			elif [ ${TYPE} = 'f' -o ${TYPE} = 'L' ] && \
+			    [ -d "${BASEDIR}/${FPATH}" ]; then
+				rm -rf "${BASEDIR}/${FPATH}"
 			fi
 		fi
 		case ${TYPE} in
@@ -2969,11 +2973,8 @@
 		d)
 			rmdir ${BASEDIR}/${FPATH}
 			;;
-		f)
-			rm ${BASEDIR}/${FPATH}
-			;;
-		L)
-			rm ${BASEDIR}/${FPATH}
+		f|L)
+			rm -f "${BASEDIR}/${FPATH}"
 			;;
 		esac
 	done < killfiles