diff --git a/src/Umbraco.Core/IO/SystemDirectories.cs b/src/Umbraco.Core/IO/SystemDirectories.cs
index 433d01c206..98fdb01ff4 100644
--- a/src/Umbraco.Core/IO/SystemDirectories.cs
+++ b/src/Umbraco.Core/IO/SystemDirectories.cs
@@ -154,7 +154,7 @@ namespace Umbraco.Core.IO
         {
             get
             {
-                return IOHelper.ReturnPath("umbracoWebservicesPath", "~/umbraco/webservices");
+                return IOHelper.ReturnPath("umbracoWebservicesPath", Umbraco.EnsureEndsWith("/") + "webservices");
             }
         }
 
diff --git a/src/Umbraco.Web.UI.Client/src/less/canvasdesigner.less b/src/Umbraco.Web.UI.Client/src/less/canvasdesigner.less
index 5bbb7caea5..52c4052975 100644
--- a/src/Umbraco.Web.UI.Client/src/less/canvasdesigner.less
+++ b/src/Umbraco.Web.UI.Client/src/less/canvasdesigner.less
@@ -3,7 +3,7 @@
 
 @font-face {
   src: url('assets/fonts/helveticons/helveticons.eot') !important;
-  src: url('assets/fonts/helveticons/helveticons.eot?#iefix') format('embedded-opentype'), url('/Umbraco/assets/fonts/helveticons/helveticons.ttf') format('truetype'), url('/Umbraco/assets/fonts/helveticons/helveticons.svg#icomoon') format('svg') !important;
+  src: url('assets/fonts/helveticons/helveticons.eot?#iefix') format('embedded-opentype'), url('assets/fonts/helveticons/helveticons.ttf') format('truetype'), url('assets/fonts/helveticons/helveticons.svg#icomoon') format('svg') !important;
 }
 
 /****************************/
diff --git a/src/Umbraco.Web/Models/ContentEditing/ContentTypeBasic.cs b/src/Umbraco.Web/Models/ContentEditing/ContentTypeBasic.cs
index 7aec396a89..795eefcc94 100644
--- a/src/Umbraco.Web/Models/ContentEditing/ContentTypeBasic.cs
+++ b/src/Umbraco.Web/Models/ContentEditing/ContentTypeBasic.cs
@@ -1,6 +1,7 @@
 using System.ComponentModel.DataAnnotations;
 using System.Runtime.Serialization;
 using Umbraco.Core;
+using Umbraco.Core.Configuration;
 using Umbraco.Core.IO;
 
 namespace Umbraco.Web.Models.ContentEditing
@@ -47,8 +48,8 @@ namespace Umbraco.Web.Models.ContentEditing
             get
             {
                 return IconIsClass
-                           ? string.Empty
-                           : IOHelper.ResolveUrl("images/umbraco/" + Icon);
+                    ? string.Empty
+                    : string.Format("{0}images/umbraco/{1}", GlobalSettings.Path.EnsureEndsWith("/"), Icon);
             }
         }
 
diff --git a/src/Umbraco.Web/Models/Trees/TreeNode.cs b/src/Umbraco.Web/Models/Trees/TreeNode.cs
index 2f64a31e83..5c8d36dd6b 100644
--- a/src/Umbraco.Web/Models/Trees/TreeNode.cs
+++ b/src/Umbraco.Web/Models/Trees/TreeNode.cs
@@ -2,6 +2,7 @@
 using Umbraco.Core.IO;
 using System.Collections.Generic;
 using Umbraco.Core;
+using Umbraco.Core.Configuration;
 using Umbraco.Web.Models.ContentEditing;
 
 namespace Umbraco.Web.Models.Trees
@@ -109,7 +110,7 @@ namespace Umbraco.Web.Models.Trees
                     return IOHelper.ResolveUrl("~" + Icon.TrimStart('~'));
 
                 //legacy icon path
-                return IOHelper.ResolveUrl("images/umbraco/" + Icon);
+                return string.Format("{0}images/umbraco/{1}", GlobalSettings.Path.EnsureEndsWith("/"), Icon);                
             }
         }