diff --git a/apps/emqx/src/emqx_listeners.erl b/apps/emqx/src/emqx_listeners.erl
index e325263c5..32599b3be 100644
--- a/apps/emqx/src/emqx_listeners.erl
+++ b/apps/emqx/src/emqx_listeners.erl
@@ -421,7 +421,7 @@ do_start_listener(Type, Name, Id, #{bind := ListenOn} = Opts) when ?ESOCKD_LISTE
     esockd:open(
         Id,
         ListenOn,
-        merge_default(esockd_opts(Id, Type, Name, Opts))
+        merge_default(esockd_opts(Id, Type, Name, Opts, _OldOpts = undefined))
     );
 %% Start MQTT/WS listener
 do_start_listener(Type, Name, Id, Opts) when ?COWBOY_LISTENER(Type) ->
@@ -465,7 +465,7 @@ do_update_listener(Type, Name, OldConf, NewConf = #{bind := ListenOn}) when
     Id = listener_id(Type, Name),
     case maps:get(bind, OldConf) of
         ListenOn ->
-            esockd:set_options({Id, ListenOn}, esockd_opts(Id, Type, Name, NewConf));
+            esockd:set_options({Id, ListenOn}, esockd_opts(Id, Type, Name, NewConf, OldConf));
         _Different ->
             %% TODO
             %% Again, we're not strictly required to drop live connections in this case.
@@ -577,7 +577,7 @@ perform_listener_change(update, {{Type, Name, ConfOld}, {_, _, ConfNew}}) ->
 perform_listener_change(stop, {Type, Name, Conf}) ->
     stop_listener(Type, Name, Conf).
 
-esockd_opts(ListenerId, Type, Name, Opts0) ->
+esockd_opts(ListenerId, Type, Name, Opts0, OldOpts) ->
     Opts1 = maps:with([acceptors, max_connections, proxy_protocol, proxy_protocol_timeout], Opts0),
     Limiter = limiter(Opts0),
     Opts2 =
@@ -609,7 +609,7 @@ esockd_opts(ListenerId, Type, Name, Opts0) ->
             tcp ->
                 Opts3#{tcp_options => tcp_opts(Opts0)};
             ssl ->
-                OptsWithCRL = inject_crl_config(Opts0),
+                OptsWithCRL = inject_crl_config(Opts0, OldOpts),
                 OptsWithSNI = inject_sni_fun(ListenerId, OptsWithCRL),
                 OptsWithRootFun = inject_root_fun(OptsWithSNI),
                 OptsWithVerifyFun = inject_verify_fun(OptsWithRootFun),
@@ -985,7 +985,7 @@ inject_sni_fun(_ListenerId, Conf) ->
     Conf.
 
 inject_crl_config(
-    Conf = #{ssl_options := #{enable_crl_check := true} = SSLOpts}
+    Conf = #{ssl_options := #{enable_crl_check := true} = SSLOpts}, _OldOpts
 ) ->
     HTTPTimeout = emqx_config:get([crl_cache, http_timeout], timer:seconds(15)),
     Conf#{
@@ -995,7 +995,16 @@ inject_crl_config(
             crl_cache => {emqx_ssl_crl_cache, {internal, [{http, HTTPTimeout}]}}
         }
     };
-inject_crl_config(Conf) ->
+inject_crl_config(#{ssl_options := SSLOpts0} = Conf0, #{} = OldOpts) ->
+    %% Note: we must set crl options to `undefined' to unset them.  Otherwise,
+    %% `esockd' will retain such options when `esockd:merge_opts/2' is called and the SSL
+    %% options were previously enabled.
+    WasEnabled = emqx_utils_maps:deep_get([ssl_options, enable_crl_check], OldOpts, false),
+    Undefine = fun(Acc, K) -> emqx_utils_maps:put_if(Acc, K, undefined, WasEnabled) end,
+    SSLOpts1 = Undefine(SSLOpts0, crl_check),
+    SSLOpts = Undefine(SSLOpts1, crl_cache),
+    Conf0#{ssl_options := SSLOpts};
+inject_crl_config(Conf, undefined = _OldOpts) ->
     Conf.
 
 maybe_unregister_ocsp_stapling_refresh(
diff --git a/apps/emqx/src/emqx_tls_lib.erl b/apps/emqx/src/emqx_tls_lib.erl
index e1de50385..1b9e89199 100644
--- a/apps/emqx/src/emqx_tls_lib.erl
+++ b/apps/emqx/src/emqx_tls_lib.erl
@@ -589,6 +589,14 @@ ensure_valid_options(Options, Versions) ->
 
 ensure_valid_options([], _, Acc) ->
     lists:reverse(Acc);
+ensure_valid_options([{K, undefined} | T], Versions, Acc) when
+    K =:= crl_check;
+    K =:= crl_cache
+->
+    %% Note: we must set crl options to `undefined' to unset them.  Otherwise,
+    %% `esockd' will retain such options when `esockd:merge_opts/2' is called and the SSL
+    %% options were previously enabled.
+    ensure_valid_options(T, Versions, [{K, undefined} | Acc]);
 ensure_valid_options([{_, undefined} | T], Versions, Acc) ->
     ensure_valid_options(T, Versions, Acc);
 ensure_valid_options([{_, ""} | T], Versions, Acc) ->
diff --git a/apps/emqx/test/emqx_crl_cache_SUITE.erl b/apps/emqx/test/emqx_crl_cache_SUITE.erl
index 1d7d0f1d5..51196439e 100644
--- a/apps/emqx/test/emqx_crl_cache_SUITE.erl
+++ b/apps/emqx/test/emqx_crl_cache_SUITE.erl
@@ -138,13 +138,14 @@ init_per_testcase(t_refresh_config = TestCase, Config) ->
     ];
 init_per_testcase(TestCase, Config) when
     TestCase =:= t_update_listener;
+    TestCase =:= t_update_listener_enable_disable;
     TestCase =:= t_validations
 ->
     ct:timetrap({seconds, 30}),
     ok = snabbkaffe:start_trace(),
     %% when running emqx standalone tests, we can't use those
     %% features.
-    case does_module_exist(emqx_management) of
+    case does_module_exist(emqx_mgmt) of
         true ->
             DataDir = ?config(data_dir, Config),
             CRLFile = filename:join([DataDir, "intermediate-revoked.crl.pem"]),
@@ -165,7 +166,7 @@ init_per_testcase(TestCase, Config) when
                     {emqx_conf, #{config => #{listeners => #{ssl => #{default => ListenerConf}}}}},
                     emqx,
                     emqx_management,
-                    {emqx_dashboard, "dashboard.listeners.http { enable = true, bind = 18083 }"}
+                    emqx_mgmt_api_test_util:emqx_dashboard()
                 ],
                 #{work_dir => emqx_cth_suite:work_dir(TestCase, Config)}
             ),
@@ -206,6 +207,7 @@ read_crl(Filename) ->
 
 end_per_testcase(TestCase, Config) when
     TestCase =:= t_update_listener;
+    TestCase =:= t_update_listener_enable_disable;
     TestCase =:= t_validations
 ->
     Skip = proplists:get_bool(skip_does_not_apply, Config),
@@ -1057,3 +1059,104 @@ do_t_validations(_Config) ->
     ),
 
     ok.
+
+%% Checks that if CRL is ever enabled and then disabled, clients can connect, even if they
+%% would otherwise not have their corresponding CRLs cached and fail with `{bad_crls,
+%% no_relevant_crls}`.
+t_update_listener_enable_disable(Config) ->
+    case proplists:get_bool(skip_does_not_apply, Config) of
+        true ->
+            ct:pal("skipping as this test does not apply in this profile"),
+            ok;
+        false ->
+            do_t_update_listener_enable_disable(Config)
+    end.
+
+do_t_update_listener_enable_disable(Config) ->
+    DataDir = ?config(data_dir, Config),
+    Keyfile = filename:join([DataDir, "server.key.pem"]),
+    Certfile = filename:join([DataDir, "server.cert.pem"]),
+    Cacertfile = filename:join([DataDir, "ca-chain.cert.pem"]),
+    ClientCert = filename:join(DataDir, "client.cert.pem"),
+    ClientKey = filename:join(DataDir, "client.key.pem"),
+
+    ListenerId = "ssl:default",
+    %% Enable CRL
+    {ok, {{_, 200, _}, _, ListenerData0}} = get_listener_via_api(ListenerId),
+    CRLConfig0 =
+        #{
+            <<"ssl_options">> =>
+                #{
+                    <<"keyfile">> => Keyfile,
+                    <<"certfile">> => Certfile,
+                    <<"cacertfile">> => Cacertfile,
+                    <<"enable_crl_check">> => true,
+                    <<"fail_if_no_peer_cert">> => true
+                }
+        },
+    ListenerData1 = emqx_utils_maps:deep_merge(ListenerData0, CRLConfig0),
+    {ok, {_, _, ListenerData2}} = update_listener_via_api(ListenerId, ListenerData1),
+    ?assertMatch(
+        #{
+            <<"ssl_options">> :=
+                #{
+                    <<"enable_crl_check">> := true,
+                    <<"verify">> := <<"verify_peer">>,
+                    <<"fail_if_no_peer_cert">> := true
+                }
+        },
+        ListenerData2
+    ),
+
+    %% Disable CRL
+    CRLConfig1 =
+        #{
+            <<"ssl_options">> =>
+                #{
+                    <<"keyfile">> => Keyfile,
+                    <<"certfile">> => Certfile,
+                    <<"cacertfile">> => Cacertfile,
+                    <<"enable_crl_check">> => false,
+                    <<"fail_if_no_peer_cert">> => true
+                }
+        },
+    ListenerData3 = emqx_utils_maps:deep_merge(ListenerData2, CRLConfig1),
+    redbug:start(
+        [
+            "esockd_server:get_listener_prop -> return",
+            "esockd_server:set_listener_prop -> return",
+            "esockd:merge_opts -> return",
+            "esockd_listener_sup:set_options -> return",
+            "emqx_listeners:inject_crl_config -> return"
+        ],
+        [{msgs, 100}]
+    ),
+    {ok, {_, _, ListenerData4}} = update_listener_via_api(ListenerId, ListenerData3),
+    ?assertMatch(
+        #{
+            <<"ssl_options">> :=
+                #{
+                    <<"enable_crl_check">> := false,
+                    <<"verify">> := <<"verify_peer">>,
+                    <<"fail_if_no_peer_cert">> := true
+                }
+        },
+        ListenerData4
+    ),
+
+    %% Now the client that would be blocked tries to connect and should now be allowed.
+    {ok, C} = emqtt:start_link([
+        {ssl, true},
+        {ssl_opts, [
+            {certfile, ClientCert},
+            {keyfile, ClientKey},
+            {verify, verify_none}
+        ]},
+        {port, 8883}
+    ]),
+    ?assertMatch({ok, _}, emqtt:connect(C)),
+    emqtt:stop(C),
+
+    ?assertNotReceive({http_get, _}),
+
+    ok.
diff --git a/changes/ce/fix-13541.en.md b/changes/ce/fix-13541.en.md
new file mode 100644
index 000000000..48013cc19
--- /dev/null
+++ b/changes/ce/fix-13541.en.md
@@ -0,0 +1 @@
+Previously, if CRL checks were ever enabled for a listener, later disabling them via the configuration would not actually disable them until the listener restarted.  This has been fixed.