diff --git a/mRemoteV1/Properties/Resources.Designer.cs b/mRemoteV1/Properties/Resources.Designer.cs
index a76bf5d6..84b6fe23 100644
--- a/mRemoteV1/Properties/Resources.Designer.cs
+++ b/mRemoteV1/Properties/Resources.Designer.cs
@@ -270,6 +270,16 @@ namespace mRemoteNG {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized resource of type System.Drawing.Bitmap.
+        /// </summary>
+        internal static System.Drawing.Bitmap ConnectedOverlay {
+            get {
+                object obj = ResourceManager.GetObject("ConnectedOverlay", resourceCulture);
+                return ((System.Drawing.Bitmap)(obj));
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized resource of type System.Drawing.Bitmap.
         /// </summary>
diff --git a/mRemoteV1/Properties/Resources.resx b/mRemoteV1/Properties/Resources.resx
index 3dcd32c7..dda31e5f 100644
--- a/mRemoteV1/Properties/Resources.resx
+++ b/mRemoteV1/Properties/Resources.resx
@@ -523,4 +523,7 @@
   <data name="exclamation" type="System.Resources.ResXFileRef, System.Windows.Forms">
     <value>..\Resources\Images\FamFamFam\exclamation.png;System.Drawing.Bitmap, System.Drawing, Version=4.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a</value>
   </data>
+  <data name="ConnectedOverlay" type="System.Resources.ResXFileRef, System.Windows.Forms">
+    <value>..\Resources\Images\ConnectedOverlay.png;System.Drawing.Bitmap, System.Drawing, Version=4.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a</value>
+  </data>
 </root>
\ No newline at end of file
diff --git a/mRemoteV1/Resources/Images/ConnectedOverlay.png b/mRemoteV1/Resources/Images/ConnectedOverlay.png
new file mode 100644
index 00000000..4baac4bb
Binary files /dev/null and b/mRemoteV1/Resources/Images/ConnectedOverlay.png differ
diff --git a/mRemoteV1/Tools/ConnectionsTreeToMenuItemsConverter.cs b/mRemoteV1/Tools/ConnectionsTreeToMenuItemsConverter.cs
index 46347eea..b36aff7a 100644
--- a/mRemoteV1/Tools/ConnectionsTreeToMenuItemsConverter.cs
+++ b/mRemoteV1/Tools/ConnectionsTreeToMenuItemsConverter.cs
@@ -6,15 +6,16 @@ using mRemoteNG.App;
 using mRemoteNG.Connection;
 using mRemoteNG.Container;
 using mRemoteNG.Tree;
+using mRemoteNG.UI.Controls;
 
 
 namespace mRemoteNG.Tools
 {
     public class ConnectionsTreeToMenuItemsConverter
     {
+        private readonly StatusImageList _statusImageList = new StatusImageList();
         public MouseEventHandler MouseUpEventHandler { get; set; }
 
-
         public IEnumerable<ToolStripDropDownItem> CreateToolStripDropDownItems(ConnectionTreeModel connectionTreeModel)
         {
             var rootNodes = connectionTreeModel.RootNodes;
@@ -49,26 +50,15 @@ namespace mRemoteNG.Tools
             var menuItem = new ToolStripMenuItem
             {
                 Text = node.Name,
-                Tag = node
+                Tag = node,
+                Image = _statusImageList.GetImage(node)
             };
 
             var nodeAsContainer = node as ContainerInfo;
             if (nodeAsContainer != null)
             {
-                menuItem.Image = Resources.Folder;
-                menuItem.Tag = nodeAsContainer;
                 AddSubMenuNodes(nodeAsContainer.Children, menuItem);
             }
-            else if (node.GetTreeNodeType() == TreeNodeType.PuttySession)
-            {
-                menuItem.Image = Resources.PuttySessions;
-                menuItem.Tag = node;
-            }
-            else if (node.GetTreeNodeType() == TreeNodeType.Connection)
-            {
-                menuItem.Image = Resources.Pause;
-                menuItem.Tag = node;
-            }
             
             menuItem.MouseUp += MouseUpEventHandler;
             return menuItem;
diff --git a/mRemoteV1/UI/Controls/ConnectionTree/ConnectionTree.Designer.cs b/mRemoteV1/UI/Controls/ConnectionTree/ConnectionTree.Designer.cs
index 2c3c0b1c..637ff174 100644
--- a/mRemoteV1/UI/Controls/ConnectionTree/ConnectionTree.Designer.cs
+++ b/mRemoteV1/UI/Controls/ConnectionTree/ConnectionTree.Designer.cs
@@ -7,19 +7,6 @@
         /// </summary>
         private System.ComponentModel.IContainer components = null;
 
-        /// <summary> 
-        /// Clean up any resources being used.
-        /// </summary>
-        /// <param name="disposing">true if managed resources should be disposed; otherwise, false.</param>
-        protected override void Dispose(bool disposing)
-        {
-            if (disposing && (components != null))
-            {
-                components.Dispose();
-            }
-            base.Dispose(disposing);
-        }
-
         #region Component Designer generated code
 
         /// <summary>
diff --git a/mRemoteV1/UI/Controls/ConnectionTree/ConnectionTree.cs b/mRemoteV1/UI/Controls/ConnectionTree/ConnectionTree.cs
index 574d74db..337ff811 100644
--- a/mRemoteV1/UI/Controls/ConnectionTree/ConnectionTree.cs
+++ b/mRemoteV1/UI/Controls/ConnectionTree/ConnectionTree.cs
@@ -20,6 +20,7 @@ namespace mRemoteNG.UI.Controls
         private ConnectionTreeModel _connectionTreeModel;
         private readonly ConnectionTreeDragAndDropHandler _dragAndDropHandler = new ConnectionTreeDragAndDropHandler();
         private readonly PuttySessionsManager _puttySessionsManager = PuttySessionsManager.Instance;
+        private readonly StatusImageList _statusImageList = new StatusImageList();
 
         public ConnectionInfo SelectedNode
         {
@@ -46,7 +47,6 @@ namespace mRemoteNG.UI.Controls
             }
         }
 
-
         public ConnectionTree()
         {
             InitializeComponent();
@@ -54,12 +54,22 @@ namespace mRemoteNG.UI.Controls
             UseOverlays = false;
         }
 
+        protected override void Dispose(bool disposing)
+        {
+            if (disposing)
+            {
+                components?.Dispose();
+                _statusImageList?.Dispose();
+            }
+            base.Dispose(disposing);
+        }
+
+
         #region ConnectionTree Setup
         private void SetupConnectionTreeView()
         {
-            var imageList = new StatusImageList();
-            SmallImageList = imageList.GetImageList();
-            AddColumns(imageList.ImageGetter);
+            SmallImageList = _statusImageList.ImageList;
+            AddColumns(_statusImageList.ImageGetter);
             LinkModelToView();
             SetupDropSink();
             SetEventHandlers();
@@ -144,7 +154,13 @@ namespace mRemoteNG.UI.Controls
         {
             //TODO for some reason property changed events are getting triggered twice for each changed property. should be just once. cant find source of duplication
             var property = propertyChangedEventArgs.PropertyName;
-            if (property != "Name" && property != "OpenConnections") return;
+            if (property != nameof(ConnectionInfo.Name)
+                && property != nameof(ConnectionInfo.OpenConnections)
+                && property != nameof(ConnectionInfo.Icon))
+            {
+                return;
+            }
+
             var senderAsConnectionInfo = sender as ConnectionInfo;
             if (senderAsConnectionInfo != null)
                 RefreshObject(senderAsConnectionInfo);
diff --git a/mRemoteV1/UI/Controls/StatusImageList.cs b/mRemoteV1/UI/Controls/StatusImageList.cs
index b5a2413d..aa8f073e 100644
--- a/mRemoteV1/UI/Controls/StatusImageList.cs
+++ b/mRemoteV1/UI/Controls/StatusImageList.cs
@@ -9,49 +9,104 @@ using mRemoteNG.Tree.Root;
 
 namespace mRemoteNG.UI.Controls
 {
-    public class StatusImageList
+    public class StatusImageList : IDisposable
     {
-        public ImageList GetImageList()
+        public ImageList ImageList { get; }
+
+        public StatusImageList()
         {
-            var imageList = new ImageList
+            ImageList = new ImageList
             {
                 ColorDepth = ColorDepth.Depth32Bit,
                 ImageSize = new Size(16, 16),
                 TransparentColor = Color.Transparent
             };
-            FillImageList(imageList);
-            return imageList;
+
+            FillImageList(ImageList);
         }
 
         public object ImageGetter(object rowObject)
         {
-            if (rowObject is RootPuttySessionsNodeInfo) return "PuttySessions";
-            if (rowObject is RootNodeInfo) return "Root";
-            if (rowObject is ContainerInfo) return "Folder";
-            var connection = rowObject as ConnectionInfo;
-            if (connection == null) return "";
-            return connection.OpenConnections.Count > 0 ? "Play" : "Pause";
+            return GetKey(rowObject as ConnectionInfo);
         }
 
-        private void FillImageList(ImageList imageList)
+        public Image GetImage(ConnectionInfo connectionInfo)
+        {
+            var key = GetKey(connectionInfo);
+            return ImageList.Images.ContainsKey(key)
+                ? ImageList.Images[key]
+                : null;
+        }
+
+        public string GetKey(ConnectionInfo connectionInfo)
+        {
+            if (connectionInfo == null) return "";
+            if (connectionInfo is RootPuttySessionsNodeInfo) return "PuttySessions";
+            if (connectionInfo is RootNodeInfo) return "Root";
+            if (connectionInfo is ContainerInfo) return "Folder";
+            
+            return GetConnectionIcon(connectionInfo);
+        }
+
+        private static string BuildConnectionIconName(string icon, bool connected)
+        {
+            var status = connected ? "Play" : "Default";
+            return $"Connection_{icon}_{status}";
+        }
+
+        private const string DefaultConnectionIcon = "";
+
+        private string GetConnectionIcon(ConnectionInfo connection)
+        {
+            if (string.IsNullOrEmpty(connection.Icon))
+            {
+                return DefaultConnectionIcon;
+            }
+
+            var connected = connection.OpenConnections.Count > 0;
+            var name = BuildConnectionIconName(connection.Icon, connected);
+            if (!ImageList.Images.ContainsKey(name))
+            {
+                var image = ConnectionIcon.FromString(connection.Icon);
+                if (image == null)
+                {
+                    return DefaultConnectionIcon;
+                }
+
+                ImageList.Images.Add(BuildConnectionIconName(connection.Icon, false), image);
+                ImageList.Images.Add(BuildConnectionIconName(connection.Icon, true), Overlay(image, Resources.ConnectedOverlay));
+
+            }
+            return name;
+        }
+
+        private static Bitmap Overlay(Icon background, Image foreground)
+        {
+            var result = background.ToBitmap();
+            using (var gr = Graphics.FromImage(result))
+            {
+                gr.DrawImage(foreground, new Rectangle(0, 0, foreground.Width, foreground.Height));
+            }
+            return result;
+        }
+
+        private static void FillImageList(ImageList imageList)
         {
             try
             {
-                imageList.Images.Add(Resources.Root);
-                imageList.Images.SetKeyName(0, "Root");
-                imageList.Images.Add(Resources.Folder);
-                imageList.Images.SetKeyName(1, "Folder");
-                imageList.Images.Add(Resources.Play);
-                imageList.Images.SetKeyName(2, "Play");
-                imageList.Images.Add(Resources.Pause);
-                imageList.Images.SetKeyName(3, "Pause");
-                imageList.Images.Add(Resources.PuttySessions);
-                imageList.Images.SetKeyName(4, "PuttySessions");
+                imageList.Images.Add("Root", Resources.Root);
+                imageList.Images.Add("Folder", Resources.Folder);
+                imageList.Images.Add("PuttySessions", Resources.PuttySessions);
             }
             catch (Exception ex)
             {
                 Runtime.MessageCollector.AddExceptionStackTrace($"Unable to fill the image list of type {nameof(StatusImageList)}", ex);
             }
         }
+
+        public void Dispose()
+        {
+            ImageList?.Dispose();
+        }
     }
 }
\ No newline at end of file
diff --git a/mRemoteV1/mRemoteV1.csproj b/mRemoteV1/mRemoteV1.csproj
index b3474d7f..bde11ba6 100644
--- a/mRemoteV1/mRemoteV1.csproj
+++ b/mRemoteV1/mRemoteV1.csproj
@@ -1194,6 +1194,7 @@
     <None Include="Resources\Images\xml.png" />
     <None Include="Resources\Images\keepass_32x32.png" />
     <None Include="Resources\Images\FamFamFam\arrow_left.png" />
+    <None Include="Resources\Images\ConnectedOverlay.png" />
     <Content Include="Resources\Images\FamFamFam\Config.png" />
     <Content Include="Resources\Images\FamFamFam\database.png" />
     <None Include="Resources\Images\FamFamFam\key.png" />