diff --git a/src/blenderbim/blenderbim/bim/module/web/operator.py b/src/blenderbim/blenderbim/bim/module/web/operator.py
index 6331c851f9..85fa952242 100644
--- a/src/blenderbim/blenderbim/bim/module/web/operator.py
+++ b/src/blenderbim/blenderbim/bim/module/web/operator.py
@@ -15,16 +15,25 @@
 #
 # You should have received a copy of the GNU General Public License
 # along with BlenderBIM Add-on.  If not, see <http://www.gnu.org/licenses/>.
+
 import os
 import bpy
+import blenderbim.core.web as core
+import blenderbim.tool as tool
 
 
 class ConnectToWebsocketServer(bpy.types.Operator):
-    bl_idname = "bim.connect_to_websocket_server"
-    bl_label = "Connect to websocket server"
-    bl_description = "Connect to a websocket server"
+    bl_idname = "bim.connect_websocket_server"
+    bl_label = "Connect/Start websocket server"
+    bl_description = "Start/Connect to a Websocket server"
 
     def execute(self, context):
+        port = context.scene.WebProperties.Webserver_port
+        if port == 0:
+            context.scene.WebProperties.Webserver_port = core.generate_port_number(tool.Web)
+
+        port = context.scene.WebProperties.Webserver_port
+        core.connect_websocket_server(tool.Web, port)
         return {"FINISHED"}
 
 
diff --git a/src/blenderbim/blenderbim/bim/module/web/prop.py b/src/blenderbim/blenderbim/bim/module/web/prop.py
index 85dedc1d79..e6b3623914 100644
--- a/src/blenderbim/blenderbim/bim/module/web/prop.py
+++ b/src/blenderbim/blenderbim/bim/module/web/prop.py
@@ -31,4 +31,4 @@ from bpy.props import (
 
 
 class WebProperties(PropertyGroup):
-    Webserver_port: StringProperty(name="Webserver Port")
+    Webserver_port: IntProperty(name="Webserver Port")
diff --git a/src/blenderbim/blenderbim/bim/module/web/ui.py b/src/blenderbim/blenderbim/bim/module/web/ui.py
index 84f8556999..17dc3bff3a 100644
--- a/src/blenderbim/blenderbim/bim/module/web/ui.py
+++ b/src/blenderbim/blenderbim/bim/module/web/ui.py
@@ -38,7 +38,7 @@ class BIM_PT_webui(Panel):
         row.prop(props, "Webserver_port", text="Webserver Port")
 
         row = layout.row()
-        row.operator("bim.connect_to_websocket_server")
+        row.operator("bim.connect_websocket_server")
 
         row = layout.row()
         row.operator("bim.kill_websocket_server")
diff --git a/src/blenderbim/blenderbim/core/web.py b/src/blenderbim/blenderbim/core/web.py
index 47e173ef3f..20cd85908d 100644
--- a/src/blenderbim/blenderbim/core/web.py
+++ b/src/blenderbim/blenderbim/core/web.py
@@ -1,2 +1,14 @@
 def open_web_ui(web):
     web.open_web_ui()
+
+
+def generate_port_number(web):
+    return web.generate_port_number()
+
+
+def connect_websocket_server(web, port):
+    # check if port already has a server listening to it
+    if web.is_port_available(port):
+        web.start_websocket_server(port)
+
+    web.connect_websocket_server(port)
diff --git a/src/blenderbim/blenderbim/tool/__init__.py b/src/blenderbim/blenderbim/tool/__init__.py
index 80ea55419f..716915f4f5 100644
--- a/src/blenderbim/blenderbim/tool/__init__.py
+++ b/src/blenderbim/blenderbim/tool/__init__.py
@@ -60,3 +60,4 @@ from blenderbim.tool.type import Type
 from blenderbim.tool.unit import Unit
 from blenderbim.tool.search import Search
 from blenderbim.tool.cost import Cost
+from blenderbim.tool.web import Web
diff --git a/src/blenderbim/blenderbim/tool/web.py b/src/blenderbim/blenderbim/tool/web.py
index 23f158c700..acf5f36638 100644
--- a/src/blenderbim/blenderbim/tool/web.py
+++ b/src/blenderbim/blenderbim/tool/web.py
@@ -1,7 +1,26 @@
+# BlenderBIM Add-on - OpenBIM Blender Add-on
+# Copyright (C) 2021 Dion Moult <dion@thinkmoult.com>, 2022 Yassine Oualid <yassine@sigmadimensions.com>
+#
+# This file is part of BlenderBIM Add-on.
+#
+# BlenderBIM Add-on is free software: you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation, either version 3 of the License, or
+# (at your option) any later version.
+#
+# BlenderBIM Add-on is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with BlenderBIM Add-on.  If not, see <http://www.gnu.org/licenses/>.
+
 import bpy
 import json
 import blenderbim.core.tool
 from typing import Union, Literal
+import socket
 import os
 import webbrowser
 import asyncio
@@ -14,7 +33,34 @@ connected_sockets = set()
 websocket_server: websockets.WebSocketServer
 ws_thread_loop = asyncio.new_event_loop()
 
+
 class Web(blenderbim.core.tool.Web):
+    @classmethod
+    def generate_port_number(cls):
+        print("Generating port number")
+        with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as s:
+            s.bind(("localhost", 0))  # Bind to a free port
+            port = s.getsockname()[1]  # get the bound port
+            print(f"Port number: {port}")
+            return port
+
+    @classmethod
+    def is_port_available(cls, port):
+        with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as s:
+            # connect_ex returns 0 if the connection succeeds
+            # indicating the port is in use
+            # otherwise returns 10061 if no server is listening
+            # indicating the port is available for use
+            return s.connect_ex(("localhost", port)) == 10061
+
+    @classmethod
+    def start_websocket_server(cls, port):
+        pass
+
+    @classmethod
+    def connect_websocket_server(cls, port):
+        pass
+
     @classmethod
     def get_webui_data(cls):
         data = {}