diff --git a/proxy/http/server/web.py b/proxy/http/server/web.py
index fafc89e58a..5892c57171 100644
--- a/proxy/http/server/web.py
+++ b/proxy/http/server/web.py
@@ -14,7 +14,7 @@
 import logging
 import mimetypes
 
-from typing import List, Optional, Dict, Union, Any, Pattern
+from typing import List, Optional, Dict, Tuple, Union, Any, Pattern
 
 from ...common.constants import DEFAULT_STATIC_SERVER_DIR
 from ...common.constants import DEFAULT_ENABLE_STATIC_SERVER, DEFAULT_ENABLE_WEB_SERVER
@@ -28,7 +28,7 @@
 from ..websocket import WebsocketFrame, websocketOpcodes
 from ..parser import HttpParser, httpParserTypes
 from ..protocols import httpProtocols
-from ..responses import NOT_FOUND_RESPONSE_PKT, NOT_IMPLEMENTED_RESPONSE_PKT, okResponse
+from ..responses import NOT_FOUND_RESPONSE_PKT, okResponse
 
 from .plugin import HttpWebServerBasePlugin
 from .protocols import httpProtocolTypes
@@ -138,65 +138,28 @@ def read_and_build_static_file_response(path: str) -> memoryview:
         except FileNotFoundError:
             return NOT_FOUND_RESPONSE_PKT
 
-    def try_upgrade(self) -> bool:
-        if self.request.has_header(b'connection') and \
-                self.request.header(b'connection').lower() == b'upgrade':
-            if self.request.has_header(b'upgrade') and \
-                    self.request.header(b'upgrade').lower() == b'websocket':
-                self.client.queue(
-                    memoryview(
-                        build_websocket_handshake_response(
-                            WebsocketFrame.key_to_accept(
-                                self.request.header(b'Sec-WebSocket-Key'),
-                            ),
-                        ),
+    def switch_to_websocket(self) -> None:
+        self.client.queue(
+            memoryview(
+                build_websocket_handshake_response(
+                    WebsocketFrame.key_to_accept(
+                        self.request.header(b'Sec-WebSocket-Key'),
                     ),
-                )
-                self.switched_protocol = httpProtocolTypes.WEBSOCKET
-            else:
-                self.client.queue(NOT_IMPLEMENTED_RESPONSE_PKT)
-                return True
-        return False
+                ),
+            ),
+        )
+        self.switched_protocol = httpProtocolTypes.WEBSOCKET
 
     def on_request_complete(self) -> Union[socket.socket, bool]:
         path = self.request.path or b'/'
-        # Routing for Http(s) requests
-        protocol = httpProtocolTypes.HTTPS \
-            if self.encryption_enabled() else \
-            httpProtocolTypes.HTTP
-        for route in self.routes[protocol]:
-            if route.match(text_(path)):
-                self.route = self.routes[protocol][route]
-                assert self.route
-                self.route.handle_request(self.request)
-                if self.request.has_header(b'connection') and \
-                        self.request.header(b'connection').lower() == b'close':
-                    return True
-                return False
-        # If a websocket route exists for the path, try upgrade
-        for route in self.routes[httpProtocolTypes.WEBSOCKET]:
-            if route.match(text_(path)):
-                self.route = self.routes[httpProtocolTypes.WEBSOCKET][route]
-                # Connection upgrade
-                teardown = self.try_upgrade()
-                if teardown:
-                    return True
-                # For upgraded connections, nothing more to do
-                if self.switched_protocol:
-                    # Invoke plugin.on_websocket_open
-                    assert self.route
-                    self.route.on_websocket_open()
-                    return False
-                break
+        # Try route
+        teardown = self._try_route(path)
+        if teardown:
+            return teardown
         # No-route found, try static serving if enabled
-        if self.flags.enable_static_server:
-            path = text_(path).split('?', 1)[0]
-            self.client.queue(
-                self.read_and_build_static_file_response(
-                    self.flags.static_server_dir + path,
-                ),
-            )
-            return True
+        teardown = self._try_static_file(path)
+        if teardown:
+            return teardown
         # Catch all unhandled web server requests, return 404
         self.client.queue(NOT_FOUND_RESPONSE_PKT)
         return True
@@ -305,3 +268,44 @@ def on_client_connection_close(self) -> None:
 
     def access_log(self, context: Dict[str, Any]) -> None:
         logger.info(DEFAULT_WEB_ACCESS_LOG_FORMAT.format_map(context))
+
+    @property
+    def _protocol(self) -> Tuple[bool, int]:
+        do_ws_upgrade = self.request.is_connection_upgrade and \
+            self.request.header(b'upgrade').lower() == b'websocket'
+        return do_ws_upgrade, httpProtocolTypes.WEBSOCKET \
+            if do_ws_upgrade \
+            else httpProtocolTypes.HTTPS \
+            if self.encryption_enabled() \
+            else httpProtocolTypes.HTTP
+
+    def _try_route(self, path: bytes) -> bool:
+        do_ws_upgrade, protocol = self._protocol
+        for route in self.routes[protocol]:
+            if route.match(text_(path)):
+                self.route = self.routes[protocol][route]
+                assert self.route
+                # Optionally, upgrade protocol
+                if do_ws_upgrade:
+                    self.switch_to_websocket()
+                    assert self.route
+                    # Invoke plugin.on_websocket_open
+                    self.route.on_websocket_open()
+                else:
+                    # Invoke plugin.handle_request
+                    self.route.handle_request(self.request)
+                    if self.request.has_header(b'connection') and \
+                            self.request.header(b'connection').lower() == b'close':
+                        return True
+        return False
+
+    def _try_static_file(self, path: bytes) -> bool:
+        if self.flags.enable_static_server:
+            path = text_(path).split('?', 1)[0]
+            self.client.queue(
+                self.read_and_build_static_file_response(
+                    self.flags.static_server_dir + path,
+                ),
+            )
+            return True
+        return False