diff --git a/src/Artemis.Core/Services/WebServer/Interfaces/IWebServerService.cs b/src/Artemis.Core/Services/WebServer/Interfaces/IWebServerService.cs
index 5cfafa6a5..b950f9f49 100644
--- a/src/Artemis.Core/Services/WebServer/Interfaces/IWebServerService.cs
+++ b/src/Artemis.Core/Services/WebServer/Interfaces/IWebServerService.cs
@@ -95,35 +95,29 @@ public interface IWebServerService : IArtemisService
     ///     Adds a new Web API controller and restarts the web server
     /// </summary>
     /// <typeparam name="T">The type of Web API controller to remove</typeparam>
-    void AddController<T>(PluginFeature feature) where T : WebApiController;
+    WebApiControllerRegistration AddController<T>(PluginFeature feature) where T : WebApiController;
 
     /// <summary>
     ///     Removes an existing Web API controller and restarts the web server
     /// </summary>
     /// <typeparam name="T">The type of Web API controller to remove</typeparam>
-    void RemoveController<T>() where T : WebApiController;
+    void RemoveController(WebApiControllerRegistration registration);
 
     /// <summary>
     ///     Adds a new EmbedIO module and restarts the web server
     /// </summary>
-    void AddModule(PluginFeature feature, Func<IWebModule> create);
+    WebModuleRegistration AddModule(PluginFeature feature, Func<IWebModule> create);
 
     /// <summary>
     ///     Removes a EmbedIO module and restarts the web server
     /// </summary>
-    void RemoveModule(Func<IWebModule> create);
+    void RemoveModule(WebModuleRegistration create);
 
     /// <summary>
     ///     Adds a new EmbedIO module and restarts the web server
     /// </summary>
     /// <typeparam name="T">The type of module to add</typeparam>
-    void AddModule<T>(PluginFeature feature) where T : IWebModule;
-
-    /// <summary>
-    ///     Removes a EmbedIO module and restarts the web server
-    /// </summary>
-    /// <typeparam name="T">The type of module to remove</typeparam>
-    void RemoveModule<T>() where T : IWebModule;
+    WebModuleRegistration AddModule<T>(PluginFeature feature) where T : IWebModule;
 
     /// <summary>
     ///     Occurs when the web server has been created and is about to start. This is the ideal place to add your own modules.
diff --git a/src/Artemis.Core/Services/WebServer/WebApiControllerRegistration.cs b/src/Artemis.Core/Services/WebServer/WebApiControllerRegistration.cs
index 1a6375a11..4a2c7bb50 100644
--- a/src/Artemis.Core/Services/WebServer/WebApiControllerRegistration.cs
+++ b/src/Artemis.Core/Services/WebServer/WebApiControllerRegistration.cs
@@ -3,26 +3,55 @@ using EmbedIO.WebApi;
 
 namespace Artemis.Core.Services;
 
-internal class WebApiControllerRegistration<T> : WebApiControllerRegistration where T : WebApiController
+/// <summary>
+/// Represents a web API controller registration.
+/// </summary>
+/// <typeparam name="T">The type of the web API controller.</typeparam>
+public class WebApiControllerRegistration<T> : WebApiControllerRegistration where T : WebApiController
 {
-    public WebApiControllerRegistration(PluginFeature feature) : base(feature, typeof(T))
+    internal WebApiControllerRegistration(IWebServerService webServerService, PluginFeature feature) : base(webServerService, feature, typeof(T))
     {
         Factory = () => feature.Plugin.Resolve<T>();
     }
 
-    public Func<T> Factory { get; set; }
-    public override object UntypedFactory => Factory;
+    internal Func<T> Factory { get; set; }
+    internal override object UntypedFactory => Factory;
 }
 
-internal abstract class WebApiControllerRegistration
+/// <summary>
+/// Represents a web API controller registration.
+/// </summary>
+public abstract class WebApiControllerRegistration
 {
-    protected WebApiControllerRegistration(PluginFeature feature, Type controllerType)
+    private readonly IWebServerService _webServerService;
+
+    /// <summary>
+    /// Creates a new instance of the <see cref="WebApiControllerRegistration"/> class.
+    /// </summary>
+    protected internal WebApiControllerRegistration(IWebServerService webServerService, PluginFeature feature, Type controllerType)
     {
+        _webServerService = webServerService;
         Feature = feature;
         ControllerType = controllerType;
+        
+        Feature.Disabled += FeatureOnDisabled;
     }
 
-    public abstract object UntypedFactory { get; }
-    public Type ControllerType { get; set; }
+    private void FeatureOnDisabled(object? sender, EventArgs e)
+    {
+        _webServerService.RemoveController(this);
+        Feature.Disabled -= FeatureOnDisabled;
+    }
+
+    internal abstract object UntypedFactory { get; }
+    
+    /// <summary>
+    /// Gets the type of the web API controller.
+    /// </summary>
+    public Type ControllerType { get; }
+    
+    /// <summary>
+    /// Gets the plugin feature that provided the web API controller.
+    /// </summary>
     public PluginFeature Feature { get; }
 }
\ No newline at end of file
diff --git a/src/Artemis.Core/Services/WebServer/WebModuleRegistration.cs b/src/Artemis.Core/Services/WebServer/WebModuleRegistration.cs
index 270a5ec4d..dca340b35 100644
--- a/src/Artemis.Core/Services/WebServer/WebModuleRegistration.cs
+++ b/src/Artemis.Core/Services/WebServer/WebModuleRegistration.cs
@@ -3,25 +3,44 @@ using EmbedIO;
 
 namespace Artemis.Core.Services;
 
-internal class WebModuleRegistration
+/// <summary>
+/// Represents a registration for a web module.
+/// </summary>
+public class WebModuleRegistration
 {
-    public WebModuleRegistration(PluginFeature feature, Type webModuleType)
+    private readonly IWebServerService _webServerService;
+
+    internal WebModuleRegistration(IWebServerService webServerService, PluginFeature feature, Type webModuleType)
     {
+        _webServerService = webServerService;
         Feature = feature ?? throw new ArgumentNullException(nameof(feature));
         WebModuleType = webModuleType ?? throw new ArgumentNullException(nameof(webModuleType));
+
+        Feature.Disabled += FeatureOnDisabled;
     }
 
-    public WebModuleRegistration(PluginFeature feature, Func<IWebModule> create)
+    internal WebModuleRegistration(IWebServerService webServerService, PluginFeature feature, Func<IWebModule> create)
     {
+        _webServerService = webServerService;
         Feature = feature ?? throw new ArgumentNullException(nameof(feature));
         Create = create ?? throw new ArgumentNullException(nameof(create));
+
+        Feature.Disabled += FeatureOnDisabled;
     }
 
+    /// <summary>
+    /// The plugin feature that provided the web module.
+    /// </summary>
     public PluginFeature Feature { get; }
-    public Type? WebModuleType { get; }
-    public Func<IWebModule>? Create { get; }
 
-    public IWebModule CreateInstance()
+    /// <summary>
+    /// The type of the web module.
+    /// </summary>
+    public Type? WebModuleType { get; }
+
+    internal Func<IWebModule>? Create { get; }
+
+    internal IWebModule CreateInstance()
     {
         if (Create != null)
             return Create();
@@ -29,4 +48,10 @@ internal class WebModuleRegistration
             return (IWebModule) Feature.Plugin.Resolve(WebModuleType);
         throw new ArtemisCoreException("WebModuleRegistration doesn't have a create function nor a web module type :(");
     }
+
+    private void FeatureOnDisabled(object? sender, EventArgs e)
+    {
+        _webServerService.RemoveModule(this);
+        Feature.Disabled -= FeatureOnDisabled;
+    }
 }
\ No newline at end of file
diff --git a/src/Artemis.Core/Services/WebServer/WebServerService.cs b/src/Artemis.Core/Services/WebServer/WebServerService.cs
index e5030c9b4..263d95315 100644
--- a/src/Artemis.Core/Services/WebServer/WebServerService.cs
+++ b/src/Artemis.Core/Services/WebServer/WebServerService.cs
@@ -39,9 +39,9 @@ internal class WebServerService : IWebServerService, IDisposable
 
         PluginsModule = new PluginsModule("/plugins");
         if (coreService.IsInitialized)
-            StartWebServer();
+            AutoStartWebServer();
         else
-            coreService.Initialized += (_, _) => StartWebServer();
+            coreService.Initialized += (sender, args) => AutoStartWebServer();
     }
 
     public event EventHandler? WebServerStopped;
@@ -138,7 +138,7 @@ internal class WebServerService : IWebServerService, IDisposable
         // Add registered controllers to the API module
         foreach (WebApiControllerRegistration registration in _controllers)
             apiModule.RegisterController(registration.ControllerType, (Func<WebApiController>) registration.UntypedFactory);
-
+        
         // Listen for state changes.
         server.StateChanged += (s, e) => _logger.Verbose("WebServer new state - {state}", e.NewState);
 
@@ -173,6 +173,18 @@ internal class WebServerService : IWebServerService, IDisposable
             OnWebServerStarted();
         }
     }
+    
+    private void AutoStartWebServer()
+    {
+        try
+        {
+            StartWebServer();
+        }
+        catch (Exception exception)
+        {
+            _logger.Warning(exception, "Failed to initially start webserver");
+        }
+    }
 
     #endregion
 
@@ -237,10 +249,6 @@ internal class WebServerService : IWebServerService, IDisposable
         return endPoint;
     }
 
-    private void HandleDataModelRequest<T>(Module<T> module, T value) where T : DataModel, new()
-    {
-    }
-
     public void RemovePluginEndPoint(PluginEndPoint endPoint)
     {
         PluginsModule.RemovePluginEndPoint(endPoint);
@@ -250,15 +258,20 @@ internal class WebServerService : IWebServerService, IDisposable
 
     #region Controller management
 
-    public void AddController<T>(PluginFeature feature) where T : WebApiController
+    public WebApiControllerRegistration AddController<T>(PluginFeature feature) where T : WebApiController
     {
-        _controllers.Add(new WebApiControllerRegistration<T>(feature));
+        if (feature == null) throw new ArgumentNullException(nameof(feature));
+
+        WebApiControllerRegistration<T> registration = new(this, feature);
+        _controllers.Add(registration);
         StartWebServer();
+
+        return registration;
     }
 
-    public void RemoveController<T>() where T : WebApiController
+    public void RemoveController(WebApiControllerRegistration registration)
     {
-        _controllers.RemoveAll(r => r.ControllerType == typeof(T));
+        _controllers.Remove(registration);
         StartWebServer();
     }
 
@@ -266,33 +279,31 @@ internal class WebServerService : IWebServerService, IDisposable
 
     #region Module management
 
-    public void AddModule(PluginFeature feature, Func<IWebModule> create)
+    public WebModuleRegistration AddModule(PluginFeature feature, Func<IWebModule> create)
     {
         if (feature == null) throw new ArgumentNullException(nameof(feature));
 
-        _modules.Add(new WebModuleRegistration(feature, create));
+        WebModuleRegistration registration = new(this, feature, create);
+        _modules.Add(registration);
         StartWebServer();
+
+        return registration;
     }
 
-    public void RemoveModule(Func<IWebModule> create)
-    {
-        _modules.RemoveAll(r => r.Create == create);
-        StartWebServer();
-    }
-
-    public void AddModule<T>(PluginFeature feature) where T : IWebModule
+    public WebModuleRegistration AddModule<T>(PluginFeature feature) where T : IWebModule
     {
         if (feature == null) throw new ArgumentNullException(nameof(feature));
-        if (_modules.Any(r => r.WebModuleType == typeof(T)))
-            return;
 
-        _modules.Add(new WebModuleRegistration(feature, typeof(T)));
+        WebModuleRegistration registration = new(this, feature, typeof(T));
+        _modules.Add(registration);
         StartWebServer();
+
+        return registration;
     }
 
-    public void RemoveModule<T>() where T : IWebModule
+    public void RemoveModule(WebModuleRegistration registration)
     {
-        _modules.RemoveAll(r => r.WebModuleType == typeof(T));
+        _modules.Remove(registration);
         StartWebServer();
     }