diff --git a/apps/vmq_server/priv/vmq_server.schema b/apps/vmq_server/priv/vmq_server.schema
index a4dc91f9f..318a6e469 100644
--- a/apps/vmq_server/priv/vmq_server.schema
+++ b/apps/vmq_server/priv/vmq_server.schema
@@ -43,6 +43,23 @@
  [{default, on},
   {datatype, flag}]}.
 
+%% Retrain subscriber mode defines if subscribers on topics with retrained flag set should wait for 
+%% a retrain server sync or process immmediatly.
+{mapping, "subscriber_retain_mode", "vmq_server.subscriber_retain_mode", [
+                                                               {default, immediate},
+                                                               {datatype, atom},
+                                                               hidden
+                                                              ]}.
+
+{translation, "vmq_server.subscriber_retain_mode",
+ fun(Conf) ->
+         case cuttlefish:conf_get("subscriber_retain_mode", Conf) of
+             immediate -> immediate;
+             syncwait -> syncwait;
+             _ -> cuttlefish:invalid("subscriber_retain_mode must be either 'immediate' or 'syncwait'!")
+         end
+ end}.
+
 %% @doc queue_type enables to change the default queue delivery behaviour from
 %% 'fifo' to 'lifo'. In order to make this work the underlying message store
 %% must deliver the messages in proper order.
diff --git a/apps/vmq_server/src/vmq_config_cli.erl b/apps/vmq_server/src/vmq_config_cli.erl
index 6dfc5d979..ccd32fd2d 100644
--- a/apps/vmq_server/src/vmq_config_cli.erl
+++ b/apps/vmq_server/src/vmq_config_cli.erl
@@ -64,7 +64,8 @@ register_config_() ->
             "suppress_lwt_on_session_takeover",
             "coordinate_registrations",
             "mqtt_connect_timeout",
-            "disconnect_on_unauthorized_publish_v3"
+            "disconnect_on_unauthorized_publish_v3",
+            "subscriber_retain_mode"
         ],
     _ = [
         clique:register_config([Key], fun register_config_callback/2)
diff --git a/apps/vmq_server/src/vmq_queue.erl b/apps/vmq_server/src/vmq_queue.erl
index 9f50c7e88..043e9f7bf 100644
--- a/apps/vmq_server/src/vmq_queue.erl
+++ b/apps/vmq_server/src/vmq_queue.erl
@@ -44,6 +44,7 @@
     notify/1,
     notify_recv/1,
     enqueue/2,
+    front/2,
     status/1,
     info/1,
     add_session/3,
@@ -109,6 +110,7 @@
     max_msgs_per_drain_step,
     waiting_call,
     opts,
+    insert_fun = enqueue,
     delayed_will ::
         {Delay :: non_neg_integer(), Fun :: function()}
         | undefined,
@@ -140,6 +142,9 @@ notify_recv(Queue) when is_pid(Queue) ->
 enqueue(Queue, Msg) when is_pid(Queue) ->
     gen_fsm:send_event(Queue, {enqueue, to_internal(Msg)}).
 
+front(Queue, Msg) when is_pid(Queue) ->
+    gen_fsm:send_event(Queue, {front, to_internal(Msg)}).
+
 enqueue_many(Queue, Msgs) when is_pid(Queue) and is_list(Msgs) ->
     NMsgs = lists:map(fun to_internal/1, Msgs),
     gen_fsm:sync_send_event(Queue, {enqueue_many, NMsgs}, infinity).
@@ -246,6 +251,12 @@ online({notify_recv, SessionPid}, #state{id = SId, sessions = Sessions} = State)
 online({enqueue, Msg}, State) ->
     _ = vmq_metrics:incr_queue_in(),
     {next_state, online, insert(Msg, State)};
+online({front, Msg}, State) ->
+    _ = vmq_metrics:incr_queue_in(),
+    State0 = State#state{insert_fun = front},
+    State1 = insert(Msg, State0),
+    State2 = State1#state{insert_fun = enqueue},
+    {next_state, online, State2};
 online(Event, State) ->
     ?LOG_ERROR("got unknown event in online state ~p", [Event]),
     {next_state, online, State}.
@@ -923,7 +934,9 @@ handle_session_down(
     end.
 
 handle_waiting_acks_and_msgs(
-    WAcks, NextMsgId, #state{id = SId, sessions = Sessions, offline = Offline} = State
+    WAcks,
+    NextMsgId,
+    #state{id = SId, sessions = Sessions, offline = Offline, insert_fun = QFun} = State
 ) ->
     %% we can only handle the last waiting acks and msgs if this is
     %% the last session active for this queue.
@@ -936,12 +949,13 @@ handle_waiting_acks_and_msgs(
                         (#deliver{msg = #vmq_msg{persisted = true} = Msg} = D, AccOffline) ->
                             queue_insert(
                                 true,
+                                QFun,
                                 D#deliver{msg = Msg#vmq_msg{persisted = false}},
                                 AccOffline,
                                 SId
                             );
                         (Msg, AccOffline) ->
-                            queue_insert(true, Msg, AccOffline, SId)
+                            queue_insert(true, QFun, Msg, AccOffline, SId)
                     end,
                     Offline,
                     WAcks
@@ -1079,45 +1093,58 @@ insert(
     %% no session online, skip QoS0 message for QoS1 or QoS2 Subscription (without QoS upgrade)
     _ = vmq_metrics:incr_queue_unhandled(1),
     State;
-insert(MsgOrRef, #state{id = SId, offline = Offline, sessions = Sessions} = State) when
+insert(
+    MsgOrRef, #state{id = SId, offline = Offline, sessions = Sessions, insert_fun = QFun} = State
+) when
     Sessions == #{}
 ->
     %% no session online, insert in offline queue
-    State#state{offline = queue_insert(true, maybe_set_expiry_ts(MsgOrRef), Offline, SId)};
+    State#state{offline = queue_insert(true, QFun, maybe_set_expiry_ts(MsgOrRef), Offline, SId)};
 %% Online Queue
-insert(MsgOrRef, #state{id = SId, deliver_mode = fanout, sessions = Sessions} = State) ->
+insert(
+    MsgOrRef,
+    #state{id = SId, deliver_mode = fanout, sessions = Sessions, insert_fun = QFun} = State
+) ->
     {NewSessions, _} = session_fold(
-        SId, fun session_insert/3, maybe_set_expiry_ts(MsgOrRef), Sessions
+        SId, QFun, fun session_insert/4, maybe_set_expiry_ts(MsgOrRef), Sessions
     ),
     State#state{sessions = NewSessions};
-insert(MsgOrRef, #state{id = SId, deliver_mode = balance, sessions = Sessions} = State) ->
+insert(
+    MsgOrRef,
+    #state{id = SId, deliver_mode = balance, sessions = Sessions, insert_fun = QFun} = State
+) ->
     Pids = maps:keys(Sessions),
     RandomPid = lists:nth(rand:uniform(maps:size(Sessions)), Pids),
     RandomSession = maps:get(RandomPid, Sessions),
-    {UpdatedSession, _} = session_insert(SId, RandomSession, maybe_set_expiry_ts(MsgOrRef)),
+    {UpdatedSession, _} = session_insert(SId, QFun, RandomSession, maybe_set_expiry_ts(MsgOrRef)),
     State#state{sessions = maps:update(RandomPid, UpdatedSession, Sessions)}.
 
-session_insert(SId, #session{status = active, queue = Q} = Session, MsgOrRef) ->
+session_insert(SId, QFun, #session{status = active, queue = Q} = Session, MsgOrRef) ->
     {
-        send(SId, Session#session{queue = queue_insert(false, MsgOrRef, Q, SId)}),
+        send(SId, Session#session{queue = queue_insert(false, QFun, MsgOrRef, Q, SId)}),
         MsgOrRef
     };
-session_insert(SId, #session{status = passive, queue = Q} = Session, MsgOrRef) ->
+session_insert(SId, QFun, #session{status = passive, queue = Q} = Session, MsgOrRef) ->
     {
-        Session#session{queue = queue_insert(false, MsgOrRef, Q, SId)},
+        Session#session{queue = queue_insert(false, QFun, MsgOrRef, Q, SId)},
         MsgOrRef
     };
-session_insert(SId, #session{status = notify, queue = Q} = Session, MsgOrRef) ->
-    {send_notification(Session#session{queue = queue_insert(false, MsgOrRef, Q, SId)}), MsgOrRef}.
+session_insert(SId, QFun, #session{status = notify, queue = Q} = Session, MsgOrRef) ->
+    {
+        send_notification(Session#session{queue = queue_insert(false, QFun, MsgOrRef, Q, SId)}),
+        MsgOrRef
+    }.
 
 %% unlimited messages accepted
-queue_insert(Offline, MsgOrRef, #queue{max = -1, size = Size, queue = Queue} = Q, SId) ->
+queue_insert(Offline, enqueue, MsgOrRef, #queue{max = -1, size = Size, queue = Queue} = Q, SId) ->
     Q#queue{queue = queue:in(maybe_offline_store(Offline, SId, MsgOrRef), Queue), size = Size + 1};
-queue_insert(Offline, MsgOrRef, #queue{ignore_max = true, size = Size, queue = Queue} = Q, SId) ->
+queue_insert(
+    Offline, enqueue, MsgOrRef, #queue{ignore_max = true, size = Size, queue = Queue} = Q, SId
+) ->
     Q#queue{queue = queue:in(maybe_offline_store(Offline, SId, MsgOrRef), Queue), size = Size + 1};
 %% tail drop in case of fifo
 queue_insert(
-    _Offline, MsgOrRef, #queue{type = fifo, max = Max, size = Size, drop = Drop} = Q, SId
+    _Offline, _QFun, MsgOrRef, #queue{type = fifo, max = Max, size = Size, drop = Drop} = Q, SId
 ) when
     Size >= Max
 ->
@@ -1128,6 +1155,7 @@ queue_insert(
 %% drop oldest in case of lifo
 queue_insert(
     Offline,
+    enqueue,
     MsgOrRef,
     #queue{type = lifo, max = Max, size = Size, queue = Queue, drop = Drop} = Q,
     SId
@@ -1142,7 +1170,11 @@ queue_insert(
         queue = queue:in(maybe_offline_store(Offline, SId, MsgOrRef), NewQueue), drop = Drop + 1
     };
 %% normal enqueue
-queue_insert(Offline, MsgOrRef, #queue{queue = Queue, size = Size} = Q, SId) ->
+queue_insert(Offline, front, MsgOrRef, #queue{queue = Queue, size = Size} = Q, SId) ->
+    Q#queue{
+        queue = queue:in_r(maybe_offline_store(Offline, SId, MsgOrRef), Queue), size = Size + 1
+    };
+queue_insert(Offline, enqueue, MsgOrRef, #queue{queue = Queue, size = Size} = Q, SId) ->
     Q#queue{queue = queue:in(maybe_offline_store(Offline, SId, MsgOrRef), Queue), size = Size + 1}.
 
 send(
@@ -1223,13 +1255,13 @@ cleanup_queue_(SId, {{value, {{qos2, _}, _}}, NewQueue}) ->
 cleanup_queue_(_, {empty, _}) ->
     ok.
 
-session_fold(SId, Fun, Acc, Map) ->
-    session_fold(SId, Fun, Acc, Map, maps:keys(Map)).
+session_fold(SId, QFun, Fun, Acc, Map) ->
+    session_fold(SId, QFun, Fun, Acc, Map, maps:keys(Map)).
 
-session_fold(SId, Fun, Acc, Map, [K | Rest]) ->
-    {NewV, NewAcc} = Fun(SId, maps:get(K, Map), Acc),
-    session_fold(SId, Fun, NewAcc, maps:update(K, NewV, Map), Rest);
-session_fold(_, _, Acc, Map, []) ->
+session_fold(SId, QFun, Fun, Acc, Map, [K | Rest]) ->
+    {NewV, NewAcc} = Fun(SId, QFun, maps:get(K, Map), Acc),
+    session_fold(SId, QFun, Fun, NewAcc, maps:update(K, NewV, Map), Rest);
+session_fold(_, _, _, Acc, Map, []) ->
     {Map, Acc}.
 
 maybe_set_expiry_timer(
diff --git a/apps/vmq_server/src/vmq_reg.erl b/apps/vmq_server/src/vmq_reg.erl
index b5b20ec6f..4cfff88a2 100644
--- a/apps/vmq_server/src/vmq_reg.erl
+++ b/apps/vmq_server/src/vmq_reg.erl
@@ -93,25 +93,25 @@ subscribe_op(SubscriberId, Topics) ->
     OldSubs = subscriptions_for_subscriber_id(SubscriberId),
     Existing = subscriptions_exist(OldSubs, Topics),
     add_subscriber(lists:usort(Topics), OldSubs, SubscriberId),
-    QoSTable =
+    {QoSTable, _Ign} =
         lists:foldl(
             fun
                 %% MQTTv4 clauses
-                ({_, {_, not_allowed}}, AccQoSTable) ->
-                    [not_allowed | AccQoSTable];
-                ({Exists, {T, QoS}}, AccQoSTable) when is_integer(QoS) ->
-                    deliver_retained(SubscriberId, T, QoS, #{}, Exists),
-                    [QoS | AccQoSTable];
+                ({_, {_, not_allowed}}, {AccQoSTable, WaitSync}) ->
+                    {[not_allowed | AccQoSTable], WaitSync};
+                ({Exists, {T, QoS}}, {AccQoSTable, WaitSync}) when is_integer(QoS) ->
+                    WaitSync0 = deliver_retained(SubscriberId, T, QoS, #{}, Exists, WaitSync),
+                    {[QoS | AccQoSTable], WaitSync0};
                 %% MQTTv5 clauses
-                ({_, {_, {not_allowed, _}}}, AccQoSTable) ->
-                    [not_allowed | AccQoSTable];
-                ({Exists, {T, {QoS, SubOpts}}}, AccQoSTable) when
+                ({_, {_, {not_allowed, _}}}, {AccQoSTable, WaitSync}) ->
+                    {[not_allowed | AccQoSTable], WaitSync};
+                ({Exists, {T, {QoS, SubOpts}}}, {AccQoSTable, WaitSync}) when
                     is_integer(QoS), is_map(SubOpts)
                 ->
-                    deliver_retained(SubscriberId, T, QoS, SubOpts, Exists),
-                    [QoS | AccQoSTable]
+                    WaitSync0 = deliver_retained(SubscriberId, T, QoS, SubOpts, Exists, WaitSync),
+                    {[QoS | AccQoSTable], WaitSync0}
             end,
-            [],
+            {[], (vmq_config:get_env(subscriber_retain_mode, immediate) == syncwait)},
             lists:zip(Existing, Topics)
         ),
     {ok, lists:reverse(QoSTable)}.
@@ -574,17 +574,28 @@ add_to_subscriber_group({Node, Group, SubscriberId, SubInfo}, SubscriberGroups,
         SubscriberGroups
     ).
 
--spec deliver_retained(subscriber_id(), topic(), qos(), subopts(), boolean()) -> 'ok'.
-deliver_retained(_, _, _, #{retain_handling := dont_send}, _) ->
+-spec deliver_retained(subscriber_id(), topic(), qos(), subopts(), boolean(), boolean()) -> 'ok'.
+deliver_retained(_, _, _, #{retain_handling := dont_send}, _, WaitSync) ->
     %% don't send, skip
-    ok;
-deliver_retained(_, _, _, #{retain_handling := send_if_new_sub}, true) ->
+    WaitSync;
+deliver_retained(_, _, _, #{retain_handling := send_if_new_sub}, true, WaitSync) ->
     %% subscription already existed, skip.
-    ok;
-deliver_retained(_SubscriberId, [<<"$share">> | _], _QoS, _SubOpts, _) ->
+    WaitSync;
+deliver_retained(_SubscriberId, [<<"$share">> | _], _QoS, _SubOpts, _, WaitSync) ->
     %% Never deliver retained messages to subscriber groups.
-    ok;
-deliver_retained({MP, _} = SubscriberId, Topic, QoS, SubOpts, _) ->
+    WaitSync;
+deliver_retained(SubscriberId, Topic, QoS, SubOpts, _, WaitSync) ->
+    deliver_retained(SubscriberId, Topic, QoS, SubOpts, WaitSync).
+
+deliver_retained({MP, _} = SubscriberId, Topic, QoS, SubOpts, WaitSync) ->
+    Ret0 =
+        case WaitSync of
+            true ->
+                timer:sleep(vmq_config:get_env(retain_persist_interval, 1000) * 2),
+                false;
+            _ ->
+                false
+        end,
     QPid = get_queue_pid(SubscriberId),
     vmq_retain_srv:match_fold(
         fun
@@ -609,7 +620,7 @@ deliver_retained({MP, _} = SubscriberId, Topic, QoS, SubOpts, _) ->
                 },
                 Msg1 = maybe_add_sub_id({QoS, SubOpts}, Msg),
                 maybe_delete_expired(ExpiryTs, MP, Topic),
-                vmq_queue:enqueue(QPid, {deliver, QoS, Msg1});
+                vmq_queue:front(QPid, {deliver, QoS, Msg1});
             ({{_M, T}, Payload}, _) when is_binary(Payload) ->
                 %% compatibility with old style retained messages.
                 Msg = #vmq_msg{
@@ -622,12 +633,13 @@ deliver_retained({MP, _} = SubscriberId, Topic, QoS, SubOpts, _) ->
                     msg_ref = vmq_mqtt_fsm_util:msg_ref(),
                     properties = #{}
                 },
-                vmq_queue:enqueue(QPid, {deliver, QoS, Msg})
+                vmq_queue:front(QPid, {deliver, QoS, Msg})
         end,
         ok,
         MP,
         Topic
-    ).
+    ),
+    Ret0.
 
 maybe_delete_expired(undefined, _, _) ->
     ok;
diff --git a/apps/vmq_server/src/vmq_server.app.src b/apps/vmq_server/src/vmq_server.app.src
index e5d77ee58..4f52d86dd 100644
--- a/apps/vmq_server/src/vmq_server.app.src
+++ b/apps/vmq_server/src/vmq_server.app.src
@@ -49,6 +49,8 @@
         {max_offline_messages, -1},
         % balance vs fanout
         {queue_deliver_mode, fanout},
+        % subscriber retain mode immediate
+        {subscriber_retain_mode, immediate},
         % fifo vs lifo
         {queue_type, fifo},
         % never
diff --git a/apps/vmq_server/test/vmq_retain_SUITE.erl b/apps/vmq_server/test/vmq_retain_SUITE.erl
index 4902a470d..10b48b7b2 100644
--- a/apps/vmq_server/test/vmq_retain_SUITE.erl
+++ b/apps/vmq_server/test/vmq_retain_SUITE.erl
@@ -28,8 +28,16 @@ end_per_suite(_Config) ->
     _Config.
 
 init_per_group(mqttv4, Config) ->
+    vmq_server_cmd:set_config(subscriber_retain_mode, immediate),
     [{protover, 4}|Config];
 init_per_group(mqttv5, Config) ->
+    vmq_server_cmd:set_config(subscriber_retain_mode, immediate),
+    [{protover, 5}|Config];
+init_per_group(mqttv4waitsync, Config) ->
+    vmq_server_cmd:set_config(subscriber_retain_mode, waitsync),
+    [{protover, 4}|Config];
+init_per_group(mqttv5waitsync, Config) ->
+    vmq_server_cmd:set_config(subscriber_retain_mode, waitsync),
     [{protover, 5}|Config].
 
 end_per_group(_Group, _Config) ->
@@ -44,7 +52,9 @@ end_per_testcase(_, Config) ->
 all() ->
     [
      {group, mqttv4},
-     {group, mqttv5}
+     {group, mqttv4waitsync},
+     {group, mqttv5},
+     {group, mqttv5waitsync}
     ].
 
 groups() ->
diff --git a/changelog.md b/changelog.md
index 6dec2a981..b618a22fc 100644
--- a/changelog.md
+++ b/changelog.md
@@ -1,3 +1,4 @@
+- New feature: Synchronized wait for retrained message store
 - Add option for a default rule ("*") in database Lua scripts, so that Clients can fallback to default ACLs.
 
 ## VerneMQ 2.0 Release Candidate