diff --git a/usr.sbin/freebsd-update/freebsd-update.sh b/usr.sbin/freebsd-update/freebsd-update.sh
--- a/usr.sbin/freebsd-update/freebsd-update.sh
+++ b/usr.sbin/freebsd-update/freebsd-update.sh
@@ -2903,7 +2903,13 @@
 	    while read FPATH TYPE OWNER GROUP PERM FLAGS HASH LINK; do
 		case ${TYPE} in
 		d)
-			# Create a directory
+			# Create a directory.  A file may change to a directory
+			# on upgrade (PR273661).  If that happens, remove the
+			# file first.
+			if [ -e "${BASEDIR}/${FPATH}" ] && \
+			    ! [ -d "${BASEDIR}/${FPATH}" ]; then
+				rm -f -- "${BASEDIR}/${FPATH}"
+			fi
 			install -d -o ${OWNER} -g ${GROUP}		\
 			    -m ${PERM} ${BASEDIR}/${FPATH}
 			;;