diff --git a/tests/sys/netpfil/pf/pfsync.sh b/tests/sys/netpfil/pf/pfsync.sh
--- a/tests/sys/netpfil/pf/pfsync.sh
+++ b/tests/sys/netpfil/pf/pfsync.sh
@@ -112,8 +112,76 @@
 	pfsynct_cleanup
 }
 
+atf_test_case "bulk" "cleanup"
+bulk_head()
+{
+	atf_set descr 'Test bulk updates'
+	atf_set require.user root
+}
+
+bulk_body()
+{
+	pfsynct_init
+
+	epair_sync=$(vnet_mkepair)
+	epair_one=$(vnet_mkepair)
+	epair_two=$(vnet_mkepair)
+
+	vnet_mkjail one ${epair_one}a ${epair_sync}a
+	vnet_mkjail two ${epair_two}a ${epair_sync}b
+
+	# pfsync interface
+	jexec one ifconfig ${epair_sync}a 192.0.2.1/24 up
+	jexec one ifconfig ${epair_one}a 198.51.100.1/24 up
+	jexec one ifconfig pfsync0 \
+		syncdev ${epair_sync}a \
+		maxupd 1\
+		up
+	jexec two ifconfig ${epair_two}a 198.51.100.2/24 up
+	jexec two ifconfig ${epair_sync}b 192.0.2.2/24 up
+
+	# Enable pf
+	jexec one pfctl -e
+	pft_set_rules one \
+		"set skip on ${epair_sync}a" \
+		"pass keep state"
+	jexec two pfctl -e
+	pft_set_rules two \
+		"set skip on ${epair_sync}b" \
+		"pass keep state"
+
+	ifconfig ${epair_one}b 198.51.100.254/24 up
+
+	# Create state prior to setting up pfsync
+	ping -c 1 -S 198.51.100.254 198.51.100.1
+
+	# Wait before setting up pfsync on two, so we don't accidentally catch
+	# the update anyway.
+	sleep 1
+
+	# Now set up pfsync in jail two
+	jexec two ifconfig pfsync0 \
+		syncdev ${epair_sync}b \
+		up
+
+	# Give pfsync time to do its thing
+	sleep 2
+
+	jexec two pfctl -s states
+	if ! jexec two pfctl -s states | grep icmp | grep 198.51.100.1 | \
+	    grep 198.51.100.2 ; then
+		atf_fail "state not found on synced host"
+	fi
+}
+
+bulk_cleanup()
+{
+	pfsynct_cleanup
+}
+
 atf_init_test_cases()
 {
 	atf_add_test_case "basic"
 	atf_add_test_case "defer"
+	atf_add_test_case "bulk"
 }