diff --git a/security/tailscale/Makefile b/security/tailscale/Makefile
index 0a336ea028c9..93a2c9db290a 100644
--- a/security/tailscale/Makefile
+++ b/security/tailscale/Makefile
@@ -1,29 +1,30 @@
 PORTNAME=	tailscale
 PORTVERSION=	1.24.2
+PORTREVISION=	1
 DISTVERSIONPREFIX=	v
 CATEGORIES=	security
 
 MAINTAINER=	ashish@FreeBSD.org
 COMMENT=	Mesh VPN that makes it easy to connect your devices
 
 LICENSE=	BSD3CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	ca_root_nss>0:security/ca_root_nss
 
 USES=		go:modules
 
 GO_MODULE=	github.com/tailscale/tailscale
 
 USE_RC_SUBR=	tailscaled
 
 GO_TARGET=	./cmd/tailscale \
 		./cmd/tailscaled
 GO_BUILDFLAGS=	-tags xversion -ldflags "\
 		-X tailscale.com/version.Long=${PORTVERSION} \
 		-X tailscale.com/version.Short=${PORTVERSION}"
 
 PLIST_FILES=	bin/tailscale  \
 		bin/tailscaled
 
 .include <bsd.port.mk>
diff --git a/security/tailscale/files/tailscaled.in b/security/tailscale/files/tailscaled.in
index b1cb480b92bc..9300e901357c 100644
--- a/security/tailscale/files/tailscaled.in
+++ b/security/tailscale/files/tailscaled.in
@@ -1,87 +1,93 @@
 #!/bin/sh
 
 # PROVIDE: tailscaled
 # REQUIRE: NETWORKING
 # KEYWORD: shutdown
 #
 # Add the following lines to /etc/rc.conf.local or /etc/rc.conf
 # to enable this service:
 #
 # tailscaled_enable (bool):	Set it to YES to enable tailscaled.
 #				Default is "NO".
 # tailscaled_port (number):	Set the port to listen on for incoming VPN packets.
 #				Default is "41641".
 # tailscaled_syslog_output_enable (bool):	Set to enable syslog output.
 #						Default is "NO". See daemon(8).
 # tailscaled_syslog_output_priority (str):	Set syslog priority if syslog enabled.
 #						Default is "info". See daemon(8).
 # tailscaled_syslog_output_facility (str):	Set syslog facility if syslog enabled.
 #						Default is "daemon". See daemon(8).
 # tailscaled_exitnode_enable (bool):	Set it to YES to announce tailscaled as
 #                                       an exit node. Default is "NO".
 
 . /etc/rc.subr
 
 name=tailscaled
 rcvar=tailscaled_enable
 
 load_rc_config $name
 
 : ${tailscaled_enable:="NO"}
 : ${tailscaled_port:="41641"}
 : ${tailscaled_exitnode_enable:="NO"}
 
 DAEMON=$(/usr/sbin/daemon 2>&1 | grep -q syslog ; echo $?)
 if [ ${DAEMON} -eq 0 ]; then
         : ${tailscaled_syslog_output_enable:="NO"}
         : ${tailscaled_syslog_output_priority:="info"}
         : ${tailscaled_syslog_output_facility:="daemon"}
         if checkyesno tailscaled_syslog_output_enable; then
                 tailscaled_syslog_output_flags="-t ${name} -T ${name}"
 
                 if [ -n "${tailscaled_syslog_output_priority}" ]; then
                         tailscaled_syslog_output_flags="${tailscaled_syslog_output_flags} -s ${tailscaled_syslog_output_priority}"
                 fi
 
                 if [ -n "${tailscaled_syslog_output_facility}" ]; then
                         tailscaled_syslog_output_flags="${tailscaled_syslog_output_flags} -l ${tailscaled_syslog_output_facility}"
                 fi
         fi
 else
         tailscaled_syslog_output_enable="NO"
         tailscaled_syslog_output_flags=""
 fi
 
 pidfile=/var/run/${name}.pid
 procname="%%PREFIX%%/bin/${name}"
 ctlname="%%PREFIX%%/bin/tailscale"
 
 # XXX: Can we have multiple interfaces?
 tailscale_tap_dev="tailscale0"
 
 start_cmd="${name}_start"
 start_postcmd="${name}_poststart"
 stop_postcmd="${name}_poststop"
 
 tailscaled_start()
 {
+	# Check for orphaned tailscale network interface
+	# And if it exists, then destroy it
+	/sbin/ifconfig ${tailscale_tap_dev} >/dev/null 2>&1 && (
+		/sbin/ifconfig ${tailscale_tap_dev} | fgrep -qw PID ||
+		/sbin/ifconfig ${tailscale_tap_dev} destroy
+	)
 	env CACHE_DIRECTORY=/var/db/tailscale /usr/sbin/daemon -f ${tailscaled_syslog_output_flags} -p ${pidfile} ${procname} --port ${tailscaled_port}
 }
 
 tailscaled_poststart()
 {
         if checkyesno tailscaled_exitnode_enable; then
 		logger -s -t tailscale "Enabling Exit node mode"
                 ${ctlname} up --advertise-exit-node
         fi
 }
 
 tailscaled_poststop()
 {
 	/sbin/ifconfig ${tailscale_tap_dev} >/dev/null 2>&1 && (
 		logger -s -t tailscaled "Destroying tailscale0 adapter"
 		/sbin/ifconfig ${tailscale_tap_dev} destroy || logger -s -t tailscaled "Failed to destroy ${tailscale_tap_dev} adapter"
 	)
 }
 
 run_rc_command "$1"