diff --git a/core/include/server.h b/core/include/server.h
index 1065d53..aefe125 100644
--- a/core/include/server.h
+++ b/core/include/server.h
@@ -228,6 +228,13 @@ class Server : public QObject {
      */
     void allowMessage();
 
+    /**
+     * @brief Method to construct and reconstruct Discord Webhook Integration.
+     *
+     * @details Constructs or rebuilds Discord Object during server startup and configuration reload.
+     */
+    void handleDiscordIntegration();
+
   signals:
 
     /**
diff --git a/core/src/commands/moderation.cpp b/core/src/commands/moderation.cpp
index d4b0433..caea60a 100644
--- a/core/src/commands/moderation.cpp
+++ b/core/src/commands/moderation.cpp
@@ -417,6 +417,7 @@ void AOClient::cmdReload(int argc, QStringList argv)
     ConfigManager::reloadSettings();
     emit server->reloadRequest(ConfigManager::serverName(), ConfigManager::serverDescription());
     server->updateHTTPAdvertiserConfig();
+    server->handleDiscordIntegration();
     sendServerMessage("Reloaded configurations");
 }
 
diff --git a/core/src/server.cpp b/core/src/server.cpp
index 775ca69..7187874 100644
--- a/core/src/server.cpp
+++ b/core/src/server.cpp
@@ -52,13 +52,7 @@ void Server::start()
         qDebug() << "Server listening on" << port;
     }
     
-    if (ConfigManager::discordWebhookEnabled()) {
-        discord = new Discord(this);
-        connect(this, &Server::modcallWebhookRequest,
-                discord, &Discord::onModcallWebhookRequested);
-        connect(this, &Server::banWebhookRequest,
-                discord, &Discord::onBanWebhookRequested);
-    }
+    handleDiscordIntegration();
 
     if (ConfigManager::advertiseHTTPServer()) {
         httpAdvertiserTimer = new QTimer(this);
@@ -289,6 +283,27 @@ void Server::allowMessage()
     can_send_ic_messages = true;
 }
 
+void Server::handleDiscordIntegration()
+{
+    if (discord != nullptr) {
+        discord->deleteLater();
+        return;
+    }
+
+    if (ConfigManager::discordWebhookEnabled()) {
+        discord = new Discord(this);
+
+        if (ConfigManager::discordModcallWebhookEnabled())
+        connect(this, &Server::modcallWebhookRequest,
+                discord, &Discord::onModcallWebhookRequested);
+
+        if (ConfigManager::discordBanWebhookEnabled())
+        connect(this, &Server::banWebhookRequest,
+                discord, &Discord::onBanWebhookRequested);
+    }
+    return;
+}
+
 Server::~Server()
 {
     for (AOClient* client : clients) {