diff --git a/ChangeLog.txt b/ChangeLog.txt
index fa0c4742..e1dc2b06 100644
--- a/ChangeLog.txt
+++ b/ChangeLog.txt
@@ -3,6 +3,8 @@
 
 Broker:
 - Fix `max_keepalive` option not being able to be set to 0.
+- Fix LWT messages not being delivered if `per_listener_settings` was set to
+  true. Closes #2314.
 
 
 2.0.12 - 2021-08-31
diff --git a/src/context.c b/src/context.c
index fc686920..d1ff0372 100644
--- a/src/context.c
+++ b/src/context.c
@@ -212,9 +212,8 @@ void context__disconnect(struct mosquitto *context)
 
 	plugin__handle_disconnect(context, -1);
 
-	net__socket_close(context);
-
 	context__send_will(context);
+	net__socket_close(context);
 	if(context->session_expiry_interval == 0){
 		/* Client session is due to be expired now */
 #ifdef WITH_BRIDGE
diff --git a/test/broker/07-will-per-listener.py b/test/broker/07-will-per-listener.py
new file mode 100755
index 00000000..43457559
--- /dev/null
+++ b/test/broker/07-will-per-listener.py
@@ -0,0 +1,58 @@
+#!/usr/bin/env python3
+
+# Test whether a client will is transmitted correctly, with per_listener_settings enabled
+
+from mosq_test_helper import *
+
+def write_config(filename, port):
+    with open(filename, 'w') as f:
+        f.write("per_listener_settings true\n")
+        f.write("listener %d\n" % (port))
+        f.write("allow_anonymous true\n")
+
+def do_test(proto_ver, clean_session):
+    rc = 1
+    mid = 53
+    connect1_packet = mosq_test.gen_connect("will-qos0-test", proto_ver=proto_ver)
+    connack1_packet = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+
+    connect2_packet = mosq_test.gen_connect("test-helper", will_topic="will/qos0/test", will_payload=b"will-message", clean_session=clean_session, proto_ver=proto_ver, session_expiry=60)
+    connack2_packet = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+
+    subscribe_packet = mosq_test.gen_subscribe(mid, "will/qos0/test", 0, proto_ver=proto_ver)
+    suback_packet = mosq_test.gen_suback(mid, 0, proto_ver=proto_ver)
+
+    publish_packet = mosq_test.gen_publish("will/qos0/test", qos=0, payload="will-message", proto_ver=proto_ver)
+
+    port = mosq_test.get_port()
+    conf_file = os.path.basename(__file__).replace('.py', '.conf')
+    write_config(conf_file, port)
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), port=port, use_conf=True)
+
+    try:
+        sock = mosq_test.do_client_connect(connect1_packet, connack1_packet, timeout=5, port=port)
+        mosq_test.do_send_receive(sock, subscribe_packet, suback_packet, "suback")
+
+        sock2 = mosq_test.do_client_connect(connect2_packet, connack2_packet, port=port, timeout=5)
+        sock2.close()
+
+        mosq_test.expect_packet(sock, "publish", publish_packet)
+        rc = 0
+
+        sock.close()
+    except mosq_test.TestError:
+        pass
+    finally:
+        os.remove(conf_file)
+        broker.terminate()
+        broker.wait()
+        (stdo, stde) = broker.communicate()
+        if rc:
+            print(stde.decode('utf-8'))
+            exit(rc)
+
+do_test(4, True)
+do_test(4, False)
+do_test(5, True)
+do_test(5, False)
+exit(0)
diff --git a/test/broker/Makefile b/test/broker/Makefile
index 04fe1314..79038a61 100644
--- a/test/broker/Makefile
+++ b/test/broker/Makefile
@@ -133,6 +133,7 @@ msg_sequence_test:
 	./07-will-null-topic.py
 	./07-will-null.py
 	./07-will-oversize-payload.py
+	./07-will-per-listener.py
 	./07-will-properties.py
 	./07-will-qos0.py
 	./07-will-reconnect-1273.py
diff --git a/test/broker/test.py b/test/broker/test.py
index c2cf5196..9bd9bb6c 100755
--- a/test/broker/test.py
+++ b/test/broker/test.py
@@ -109,6 +109,7 @@ tests = [
     (1, './07-will-null-topic.py'),
     (1, './07-will-null.py'),
     (1, './07-will-oversize-payload.py'),
+    (1, './07-will-per-listener.py'),
     (1, './07-will-properties.py'),
     (1, './07-will-qos0.py'),
     (1, './07-will-reconnect-1273.py'),