diff --git a/apps/emqx/src/emqx_persistent_session_ds.erl b/apps/emqx/src/emqx_persistent_session_ds.erl
index 2cbf65b47..3517d6b73 100644
--- a/apps/emqx/src/emqx_persistent_session_ds.erl
+++ b/apps/emqx/src/emqx_persistent_session_ds.erl
@@ -123,7 +123,12 @@
 -define(TIMER_PULL, timer_pull).
 -define(TIMER_GET_STREAMS, timer_get_streams).
 -define(TIMER_BUMP_LAST_ALIVE_AT, timer_bump_last_alive_at).
--type timer() :: ?TIMER_PULL | ?TIMER_GET_STREAMS | ?TIMER_BUMP_LAST_ALIVE_AT.
+-define(TIMER_RETRY_REPLAY, timer_retry_replay).
+
+-type timer() :: ?TIMER_PULL | ?TIMER_GET_STREAMS | ?TIMER_BUMP_LAST_ALIVE_AT | ?TIMER_RETRY_REPLAY.
+
+%% TODO: Needs configuration?
+-define(TIMEOUT_RETRY_REPLAY, 1000).
 
 -type session() :: #{
     %% Client ID
@@ -134,6 +139,8 @@
     s := emqx_persistent_session_ds_state:t(),
     %% Buffer:
     inflight := emqx_persistent_session_ds_inflight:t(),
+    %% In-progress replay:
+    replay => [{_StreamKey, stream_state()}, ...],
     %% Timers:
     timer() => reference()
 }.
@@ -454,7 +461,7 @@ handle_timeout(
     ClientInfo,
     ?TIMER_PULL,
     Session0
-) ->
+) when not is_map_key(replay, Session0) ->
     {Publishes, Session1} = drain_buffer(fetch_new_messages(Session0, ClientInfo)),
     Timeout =
         case Publishes of
@@ -465,6 +472,12 @@ handle_timeout(
         end,
     Session = emqx_session:ensure_timer(?TIMER_PULL, Timeout, Session1),
     {ok, Publishes, Session};
+handle_timeout(ClientInfo, ?TIMER_PULL, Session0 = #{replay := [_ | _]}) ->
+    Session = replay_streams(Session0, ClientInfo),
+    {ok, [], Session};
+handle_timeout(ClientInfo, ?TIMER_RETRY_REPLAY, Session0) ->
+    Session = replay_streams(Session0, ClientInfo),
+    {ok, [], Session};
 handle_timeout(_ClientInfo, ?TIMER_GET_STREAMS, Session0 = #{s := S0}) ->
     S1 = emqx_persistent_session_ds_subs:gc(S0),
     S = emqx_persistent_session_ds_stream_scheduler:renew_streams(S1),
@@ -503,30 +516,44 @@ bump_last_alive(S0) ->
     {ok, replies(), session()}.
 replay(ClientInfo, [], Session0 = #{s := S0}) ->
     Streams = emqx_persistent_session_ds_stream_scheduler:find_replay_streams(S0),
-    Session = lists:foldl(
-        fun({_StreamKey, Stream}, SessionAcc) ->
-            replay_batch(Stream, SessionAcc, ClientInfo)
-        end,
-        Session0,
-        Streams
-    ),
+    Session = replay_streams(Session0#{replay => Streams}, ClientInfo),
+    {ok, [], Session}.
+
+replay_streams(Session0 = #{replay := [{_StreamKey, Srs0} | Rest]}, ClientInfo) ->
+    case replay_batch(Srs0, Session0, ClientInfo) of
+        Session = #{} ->
+            replay_streams(Session#{replay := Rest}, ClientInfo);
+        {error, _, _} ->
+            emqx_session:ensure_timer(?TIMER_RETRY_REPLAY, ?TIMEOUT_RETRY_REPLAY, Session0)
+    end;
+replay_streams(Session0 = #{replay := []}, _ClientInfo) ->
+    Session = maps:remove(replay, Session0),
     %% Note: we filled the buffer with the historical messages, and
     %% from now on we'll rely on the normal inflight/flow control
     %% mechanisms to replay them:
-    {ok, [], pull_now(Session)}.
+    pull_now(Session).
 
 -spec replay_batch(stream_state(), session(), clientinfo()) -> session().
-replay_batch(Srs0, Session, ClientInfo) ->
+replay_batch(Srs0, Session0, ClientInfo) ->
     #srs{batch_size = BatchSize} = Srs0,
-    %% TODO: retry on errors:
-    {Srs, Inflight} = enqueue_batch(true, BatchSize, Srs0, Session, ClientInfo),
-    %% Assert:
-    Srs =:= Srs0 orelse
-        ?tp(warning, emqx_persistent_session_ds_replay_inconsistency, #{
-            expected => Srs0,
-            got => Srs
-        }),
-    Session#{inflight => Inflight}.
+    case enqueue_batch(true, BatchSize, Srs0, Session0, ClientInfo) of
+        {ok, Srs, Session} ->
+            %% Assert:
+            Srs =:= Srs0 orelse
+                ?tp(warning, emqx_persistent_session_ds_replay_inconsistency, #{
+                    expected => Srs0,
+                    got => Srs
+                }),
+            Session;
+        {error, recoverable, Reason} = Error ->
+            ?SLOG(warning, #{
+                msg => "failed_to_fetch_replay_batch",
+                stream => Srs0,
+                reason => Reason,
+                class => recoverable
+            }),
+            Error
+    end.
 
 %%--------------------------------------------------------------------
 
@@ -743,7 +770,7 @@ fetch_new_messages([I | Streams], Session0 = #{inflight := Inflight}, ClientInfo
             fetch_new_messages(Streams, Session, ClientInfo)
     end.
 
-new_batch({StreamKey, Srs0}, BatchSize, Session = #{s := S0}, ClientInfo) ->
+new_batch({StreamKey, Srs0}, BatchSize, Session0 = #{s := S0}, ClientInfo) ->
     SN1 = emqx_persistent_session_ds_state:get_seqno(?next(?QOS_1), S0),
     SN2 = emqx_persistent_session_ds_state:get_seqno(?next(?QOS_2), S0),
     Srs1 = Srs0#srs{
@@ -753,11 +780,30 @@ new_batch({StreamKey, Srs0}, BatchSize, Session = #{s := S0}, ClientInfo) ->
         last_seqno_qos1 = SN1,
         last_seqno_qos2 = SN2
     },
-    {Srs, Inflight} = enqueue_batch(false, BatchSize, Srs1, Session, ClientInfo),
-    S1 = emqx_persistent_session_ds_state:put_seqno(?next(?QOS_1), Srs#srs.last_seqno_qos1, S0),
-    S2 = emqx_persistent_session_ds_state:put_seqno(?next(?QOS_2), Srs#srs.last_seqno_qos2, S1),
-    S = emqx_persistent_session_ds_state:put_stream(StreamKey, Srs, S2),
-    Session#{s => S, inflight => Inflight}.
+    case enqueue_batch(false, BatchSize, Srs1, Session0, ClientInfo) of
+        {ok, Srs, Session} ->
+            S1 = emqx_persistent_session_ds_state:put_seqno(
+                ?next(?QOS_1),
+                Srs#srs.last_seqno_qos1,
+                S0
+            ),
+            S2 = emqx_persistent_session_ds_state:put_seqno(
+                ?next(?QOS_2),
+                Srs#srs.last_seqno_qos2,
+                S1
+            ),
+            S = emqx_persistent_session_ds_state:put_stream(StreamKey, Srs, S2),
+            Session#{s => S};
+        {error, Class, Reason} ->
+            %% TODO: Handle unrecoverable error.
+            ?SLOG(info, #{
+                msg => "failed_to_fetch_batch",
+                stream => Srs1,
+                reason => Reason,
+                class => Class
+            }),
+            Session0
+    end.
 
 enqueue_batch(IsReplay, BatchSize, Srs0, Session = #{inflight := Inflight0}, ClientInfo) ->
     #srs{
@@ -786,13 +832,13 @@ enqueue_batch(IsReplay, BatchSize, Srs0, Session = #{inflight := Inflight0}, Cli
                 last_seqno_qos1 = LastSeqnoQos1,
                 last_seqno_qos2 = LastSeqnoQos2
             },
-            {Srs, Inflight};
+            {ok, Srs, Session#{inflight := Inflight}};
         {ok, end_of_stream} ->
             %% No new messages; just update the end iterator:
-            {Srs0#srs{it_begin = ItBegin, it_end = end_of_stream, batch_size = 0}, Inflight0};
-        {error, _} when not IsReplay ->
-            ?SLOG(info, #{msg => "failed_to_fetch_batch", iterator => ItBegin}),
-            {Srs0, Inflight0}
+            Srs = Srs0#srs{it_begin = ItBegin, it_end = end_of_stream, batch_size = 0},
+            {ok, Srs, Session#{inflight := Inflight0}};
+        {error, _, _} = Error ->
+            Error
     end.
 
 %% key_of_iter(#{3 := #{3 := #{5 := K}}}) ->