diff --git a/src/emqx_channel.erl b/src/emqx_channel.erl
index 939be4270..c49299c58 100644
--- a/src/emqx_channel.erl
+++ b/src/emqx_channel.erl
@@ -735,8 +735,8 @@ handle_deliver(Delivers, Channel = #channel{
     %% NOTE: Order is important here. While the takeover is in
     %% progress, the session cannot enqueue messages, since it already
     %% passed on the queue to the new connection in the session state.
-    NPendings = lists:append(Pendings,
-        ignore_local(ClientInfo, maybe_nack(Delivers), ClientId, Session)),
+    NDelivers = ignore_local(ClientInfo, maybe_discard_shared_delivers(Delivers), ClientId, Session),
+    NPendings = lists:append(Pendings, NDelivers),
     {ok, Channel#channel{pendings = NPendings}};
 
 handle_deliver(Delivers, Channel = #channel{
@@ -744,8 +744,8 @@ handle_deliver(Delivers, Channel = #channel{
         takeover   = false,
         session    = Session,
         clientinfo = #{clientid := ClientId} = ClientInfo}) ->
-    NSession = emqx_session:enqueue(ClientInfo,
-        ignore_local(ClientInfo, maybe_nack(Delivers), ClientId, Session), Session),
+    NDelivers = ignore_local(ClientInfo, maybe_discard_shared_delivers(Delivers), ClientId, Session),
+    NSession = emqx_session:enqueue(ClientInfo, NDelivers, Session),
     {ok, Channel#channel{session = NSession}};
 
 handle_deliver(Delivers, Channel = #channel{
@@ -776,12 +776,23 @@ ignore_local(ClientInfo, Delivers, Subscriber, Session) ->
                     end, Delivers).
 
 %% Nack delivers from shared subscription
-maybe_nack(Delivers) ->
-    lists:filter(fun not_nacked/1, Delivers).
-
-not_nacked({deliver, _Topic, Msg}) ->
-    not (emqx_shared_sub:is_ack_required(Msg)
-         andalso (ok == emqx_shared_sub:nack_no_connection(Msg))).
+maybe_discard_shared_delivers(Delivers) ->
+    lists:filtermap(
+      fun({deliver, Topic, Msg}) ->
+              case emqx_shared_sub:is_ack_required(Msg) of
+                  false ->
+                      true;
+                  true ->
+                      case emqx_shared_sub:is_retry_dispatch(Msg) of
+                          true ->
+                              %% force enqueue the retried shared deliver
+                              {true, {deliver, Topic, emqx_shared_sub:maybe_ack(Msg)}};
+                          false ->
+                              ok = emqx_shared_sub:nack_no_connection(Msg),
+                              false
+                      end
+              end
+      end, Delivers).
 
 %%--------------------------------------------------------------------
 %% Handle outgoing packet
diff --git a/src/emqx_shared_sub.erl b/src/emqx_shared_sub.erl
index 337d63d15..3b533d9d3 100644
--- a/src/emqx_shared_sub.erl
+++ b/src/emqx_shared_sub.erl
@@ -46,6 +46,7 @@
         , maybe_nack_dropped/1
         , nack_no_connection/1
         , is_ack_required/1
+        , is_retry_dispatch/1
         , get_group/1
         ]).
 
@@ -239,6 +240,13 @@ get_group(Msg) ->
 -spec(is_ack_required(emqx_types:message()) -> boolean()).
 is_ack_required(Msg) -> ?NO_ACK =/= get_group_ack(Msg).
 
+-spec(is_retry_dispatch(emqx_types:message()) -> boolean()).
+is_retry_dispatch(Msg) ->
+    case get_group_ack(Msg) of
+        {_Sender, {retry, _Group, _Ref}} -> true;
+        _ -> false
+    end.
+
 %% @doc Negative ack dropped message due to inflight window or message queue being full.
 -spec(maybe_nack_dropped(emqx_types:message()) -> store | drop).
 maybe_nack_dropped(Msg) ->
@@ -280,10 +288,15 @@ maybe_ack(Msg) ->
             Msg;
         Ack ->
             {Sender, Ref} = fetch_sender_ref(Ack),
-            Sender ! {Ref, ?ACK},
+            ack(Sender, Ref),
             without_group_ack(Msg)
     end.
 
+-spec(ack(pid(), reference()) -> ok).
+ack(Sender, Ref) ->
+    Sender ! {Ref, ?ACK},
+    ok.
+
 fetch_sender_ref({Sender, {_Type, _Group, Ref}}) -> {Sender, Ref};
 %% These clauses are for backward compatibility
 fetch_sender_ref({Sender, Ref}) -> {Sender, Ref}.