diff --git a/tests/sys/netpfil/pf/route_to.sh b/tests/sys/netpfil/pf/route_to.sh
index a714e0588a9f..33c180ce82cf 100755
--- a/tests/sys/netpfil/pf/route_to.sh
+++ b/tests/sys/netpfil/pf/route_to.sh
@@ -1,81 +1,164 @@
 # $FreeBSD$
 
 . $(atf_get_srcdir)/utils.subr
 
 atf_test_case "v4" "cleanup"
 v4_head()
 {
 	atf_set descr 'Basic route-to test'
 	atf_set require.user root
 }
 
 v4_body()
 {
 	pft_init
 
 	epair_send=$(vnet_mkepair)
 	ifconfig ${epair_send}a 192.0.2.1/24 up
 	epair_route=$(vnet_mkepair)
 	ifconfig ${epair_route}a 203.0.113.1/24 up
 
 	vnet_mkjail alcatraz ${epair_send}b ${epair_route}b
 	jexec alcatraz ifconfig ${epair_send}b 192.0.2.2/24 up
 	jexec alcatraz ifconfig ${epair_route}b 203.0.113.2/24 up
 	jexec alcatraz route add -net 198.51.100.0/24 192.0.2.1
 	jexec alcatraz pfctl -e
 
 	# Attempt to provoke PR 228782
 	pft_set_rules alcatraz "block all" "pass user 2" \
 		"pass out route-to (${epair_route}b 203.0.113.1) from 192.0.2.2 to 198.51.100.1 no state"
 	jexec alcatraz nc -w 3 -s 192.0.2.2 198.51.100.1 22
 
 	# atf wants us to not return an error, but our netcat will fail
 	true
 }
 
 v4_cleanup()
 {
 	pft_cleanup
 }
 
 atf_test_case "v6" "cleanup"
 v6_head()
 {
 	atf_set descr 'Basic route-to test (IPv6)'
 	atf_set require.user root
 }
 
 v6_body()
 {
 	pft_init
 
 	epair_send=$(vnet_mkepair)
 	ifconfig ${epair_send}a inet6 2001:db8:42::1/64 up no_dad -ifdisabled
 	epair_route=$(vnet_mkepair)
 	ifconfig ${epair_route}a inet6 2001:db8:43::1/64 up no_dad -ifdisabled
 
 	vnet_mkjail alcatraz ${epair_send}b ${epair_route}b
 	jexec alcatraz ifconfig ${epair_send}b inet6 2001:db8:42::2/64 up no_dad
 	jexec alcatraz ifconfig ${epair_route}b inet6 2001:db8:43::2/64 up no_dad
 	jexec alcatraz route add -6 2001:db8:666::/64 2001:db8:42::2
 	jexec alcatraz pfctl -e
 
 	# Attempt to provoke PR 228782
 	pft_set_rules alcatraz "block all" "pass user 2" \
 		"pass out route-to (${epair_route}b 2001:db8:43::1) from 2001:db8:42::2 to 2001:db8:666::1 no state"
 	jexec alcatraz nc -6 -w 3 -s 2001:db8:42::2 2001:db8:666::1 22
 
 	# atf wants us to not return an error, but our netcat will fail
 	true
 }
 
 v6_cleanup()
 {
 	pft_cleanup
 }
 
+atf_test_case "multiwan" "cleanup"
+multiwan_head()
+{
+	atf_set descr 'Multi-WAN redirection / reply-to test'
+	atf_set require.user root
+}
+
+multiwan_body()
+{
+	pft_init
+
+	epair_one=$(vnet_mkepair)
+	epair_two=$(vnet_mkepair)
+	epair_cl_one=$(vnet_mkepair)
+	epair_cl_two=$(vnet_mkepair)
+
+	vnet_mkjail srv ${epair_one}b ${epair_two}b
+	vnet_mkjail wan_one ${epair_one}a ${epair_cl_one}b
+	vnet_mkjail wan_two ${epair_two}a ${epair_cl_two}b
+	vnet_mkjail client ${epair_cl_one}a ${epair_cl_two}a
+
+	jexec client ifconfig ${epair_cl_one}a 203.0.113.1/25
+	jexec wan_one ifconfig ${epair_cl_one}b 203.0.113.2/25
+	jexec wan_one ifconfig ${epair_one}a 192.0.2.1/24 up
+	jexec wan_one sysctl net.inet.ip.forwarding=1
+	jexec srv ifconfig ${epair_one}b 192.0.2.2/24 up
+	jexec client route add 192.0.2.0/24 203.0.113.2
+
+	jexec client ifconfig ${epair_cl_two}a 203.0.113.128/25
+	jexec wan_two ifconfig ${epair_cl_two}b 203.0.113.129/25
+	jexec wan_two ifconfig ${epair_two}a 198.51.100.1/24 up
+	jexec wan_two sysctl net.inet.ip.forwarding=1
+	jexec srv ifconfig ${epair_two}b 198.51.100.2/24 up
+	jexec client route add 198.51.100.0/24 203.0.113.129
+
+	jexec srv ifconfig lo0 127.0.0.1/8 up
+	jexec srv route add default 192.0.2.1
+	jexec srv sysctl net.inet.ip.forwarding=1
+
+	# Run echo server in srv jail
+	jexec srv /usr/sbin/inetd -p multiwan.pid $(atf_get_srcdir)/echo_inetd.conf
+
+	jexec srv pfctl -e
+	pft_set_rules srv \
+		"nat on ${epair_one}b inet from 127.0.0.0/8 to any -> (${epair_one}b)" \
+		"nat on ${epair_two}b inet from 127.0.0.0/8 to any -> (${epair_two}b)" \
+		"rdr on ${epair_one}b inet proto tcp from any to 192.0.2.2 port 7 -> 127.0.0.1 port 7" \
+		"rdr on ${epair_two}b inet proto tcp from any to 198.51.100.2 port 7 -> 127.0.0.1 port 7" \
+		"block in"	\
+		"block out"	\
+		"pass in quick on ${epair_one}b reply-to (${epair_one}b 192.0.2.1) inet proto tcp from any to 127.0.0.1 port 7" \
+		"pass in quick on ${epair_two}b reply-to (${epair_two}b 198.51.100.1) inet proto tcp from any to 127.0.0.1 port 7"
+
+	# These will always succeed, because we don't change interface to route
+	# correctly here.
+	result=$(echo "one" | jexec wan_one nc -N -w 3 192.0.2.2 7)
+	if [ "${result}" != "one" ]; then
+		atf_fail "Redirect on one failed"
+	fi
+	result=$(echo "two" | jexec wan_two nc -N -w 3 198.51.100.2 7)
+	if [ "${result}" != "two" ]; then
+		atf_fail "Redirect on two failed"
+	fi
+
+	result=$(echo "one" | jexec client nc -N -w 3 192.0.2.2 7)
+	if [ "${result}" != "one" ]; then
+		atf_fail "Redirect from client on one failed"
+	fi
+
+	# This should trigger the issue fixed in 829a69db855b48ff7e8242b95e193a0783c489d9
+	result=$(echo "two" | jexec client nc -N -w 3 198.51.100.2 7)
+	if [ "${result}" != "two" ]; then
+		atf_fail "Redirect from client on two failed"
+	fi
+}
+
+multiwan_cleanup()
+{
+	rm -f multiwan.pid
+	pft_cleanup
+}
+
 atf_init_test_cases()
 {
 	atf_add_test_case "v4"
 	atf_add_test_case "v6"
+	atf_add_test_case "multiwan"
 }