diff --git a/errbot/core_plugins/wsview.py b/errbot/core_plugins/wsview.py
index 589ef8267..c63cd0021 100644
--- a/errbot/core_plugins/wsview.py
+++ b/errbot/core_plugins/wsview.py
@@ -46,16 +46,19 @@ def route(obj):
                 func.__name__ + "_" + "_".join(verbs), func, form_param, raw
             )
 
-            # Change existing rule.
+            # Update existing rule if present; otherwise register a new rule
             for rule in flask_app.url_map._rules:
                 if rule.rule == uri_rule:
                     flask_app.view_functions[rule.endpoint] = callable_view
-                    return
-
-            # Add a new rule
-            flask_app.add_url_rule(
-                uri_rule, view_func=callable_view, methods=verbs, strict_slashes=False
-            )
+                    break
+            else:
+                flask_app._got_first_request = False
+                flask_app.add_url_rule(
+                    uri_rule,
+                    view_func=callable_view,
+                    methods=verbs,
+                    strict_slashes=False,
+                )
 
 
 class WebView(View):
diff --git a/tests/webhooks_test.py b/tests/webhooks_test.py
index de32e6b03..d8ed11db8 100644
--- a/tests/webhooks_test.py
+++ b/tests/webhooks_test.py
@@ -210,3 +210,71 @@ def test_lambda_webhook(webhook_testbot):
         requests.post("http://localhost:{}/lambda".format(WEBSERVER_PORT)).status_code
         == 200
     )
+
+
+def test_route_webhook_after_first_request(webhook_testbot):
+    from errbot import BotPlugin, webhook
+    from errbot.core_plugins.wsview import route
+
+    assert (
+        requests.post(
+            f"http://localhost:{WEBSERVER_PORT}/echo",
+            JSONOBJECT,
+        ).status_code
+        == 200
+    )
+
+    class DynamicPlugin(BotPlugin):
+        @webhook("/dynamic/late_webhook")
+        def late_webhook(self, payload):
+            return "late webhook ok"
+
+        @webhook("/dynamic/late_webhook2")
+        def late_webhook2(self, payload):
+            return "late webhook2 ok"
+
+    plugin = DynamicPlugin(webhook_testbot.bot)
+    route(plugin)
+
+    resp = requests.post(f"http://localhost:{WEBSERVER_PORT}/dynamic/late_webhook")
+    assert resp.status_code == 200
+    assert resp.text == "late webhook ok"
+
+    resp2 = requests.post(f"http://localhost:{WEBSERVER_PORT}/dynamic/late_webhook2")
+    assert resp2.status_code == 200
+    assert resp2.text == "late webhook2 ok"
+
+
+def test_route_webhook_reload_updates_all_methods(webhook_testbot):
+    from errbot import BotPlugin, webhook
+    from errbot.core_plugins.wsview import route
+
+    class MultiWebhookPlugin(BotPlugin):
+        @webhook("/reload/w1")
+        def w1(self, payload):
+            return "v1_w1"
+
+        @webhook("/reload/w2")
+        def w2(self, payload):
+            return "v1_w2"
+
+    plugin_v1 = MultiWebhookPlugin(webhook_testbot.bot)
+    route(plugin_v1)
+
+    assert requests.post(f"http://localhost:{WEBSERVER_PORT}/reload/w1").text == "v1_w1"
+    assert requests.post(f"http://localhost:{WEBSERVER_PORT}/reload/w2").text == "v1_w2"
+
+    class MultiWebhookPluginV2(BotPlugin):
+        @webhook("/reload/w1")
+        def w1(self, payload):
+            return "v2_w1"
+
+        @webhook("/reload/w2")
+        def w2(self, payload):
+            return "v2_w2"
+
+    plugin_v2 = MultiWebhookPluginV2(webhook_testbot.bot)
+    route(plugin_v2)
+
+    assert requests.post(f"http://localhost:{WEBSERVER_PORT}/reload/w1").text == "v2_w1"
+    assert requests.post(f"http://localhost:{WEBSERVER_PORT}/reload/w2").text == "v2_w2"