diff --git a/src/Umbraco.Web/Strategies/DataTypes/LegacyUploadFieldWorkaround.cs b/src/Umbraco.Web/Strategies/DataTypes/LegacyUploadFieldWorkaround.cs
index aaac98c89c..443e27ef13 100644
--- a/src/Umbraco.Web/Strategies/DataTypes/LegacyUploadFieldWorkaround.cs
+++ b/src/Umbraco.Web/Strategies/DataTypes/LegacyUploadFieldWorkaround.cs
@@ -1,13 +1,10 @@
 using System;
 using System.Drawing;
 using System.Globalization;
-using System.IO;
 using System.Linq;
-using System.Web;
 using System.Xml;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.IO;
-using Umbraco.Core.Models;
 using umbraco.interfaces;
 
 namespace Umbraco.Web.Strategies.DataTypes
@@ -36,7 +33,7 @@ namespace Umbraco.Web.Strategies.DataTypes
 					return;
 
 
-				FillProperties(sender.Content, property);
+				FillProperties(sender, property);
 			}
 		}
 
@@ -49,11 +46,11 @@ namespace Umbraco.Web.Strategies.DataTypes
 					return;
 
 
-				FillProperties(sender.MediaItem, property);
+				FillProperties(sender, property);
 			}
 		}
 
-		private void FillProperties(IContentBase content, global::umbraco.cms.businesslogic.property.Property property)
+        private void FillProperties(global::umbraco.cms.businesslogic.Content content, global::umbraco.cms.businesslogic.property.Property property)
 		{
 			XmlNode uploadFieldConfigNode = global::umbraco.UmbracoSettings.ImageAutoFillImageProperties.SelectSingleNode(string.Format("uploadField [@alias = \"{0}\"]", property.PropertyType.Alias));
 
@@ -87,14 +84,14 @@ namespace Umbraco.Web.Strategies.DataTypes
 			}
 		}
 
-		private void UpdateProperty(XmlNode uploadFieldConfigNode, IContentBase content, string propertyAlias, object propertyValue)
+        private void UpdateProperty(XmlNode uploadFieldConfigNode, global::umbraco.cms.businesslogic.Content content, string propertyAlias, object propertyValue)
 		{
 			XmlNode propertyNode = uploadFieldConfigNode.SelectSingleNode(propertyAlias);
 			if (propertyNode != null && !String.IsNullOrEmpty(propertyNode.FirstChild.Value))
 			{
-				if (content.Properties.Contains(propertyNode.FirstChild.Value) && content.Properties[propertyNode.FirstChild.Value] != null)
+                if (content.GenericProperties.Any(x => x.PropertyType.Alias == propertyNode.FirstChild.Value) && content.getProperty(propertyNode.FirstChild.Value) != null)
 				{
-					content.SetValue(propertyNode.FirstChild.Value, propertyValue);
+				    content.getProperty(propertyNode.FirstChild.Value).Value = propertyValue;
 				}
 			}
 		}
diff --git a/src/umbraco.cms/businesslogic/media/Media.cs b/src/umbraco.cms/businesslogic/media/Media.cs
index b7ca32efee..be489dae01 100644
--- a/src/umbraco.cms/businesslogic/media/Media.cs
+++ b/src/umbraco.cms/businesslogic/media/Media.cs
@@ -303,6 +303,9 @@ namespace umbraco.cms.businesslogic.media
         [Obsolete("Obsolete, Use Umbraco.Core.Services.MediaService.Save()", false)]
         public override void Save()
         {
+            SaveEventArgs e = new SaveEventArgs();
+            FireBeforeSave(e);
+
             foreach (var property in GenericProperties)
             {
                 if (property.Value == null)
@@ -311,9 +314,6 @@ namespace umbraco.cms.businesslogic.media
                 MediaItem.SetValue(property.PropertyType.Alias, property.Value);
             }
             
-            SaveEventArgs e = new SaveEventArgs();
-            FireBeforeSave(e);
-            
             if (!e.Cancel)
             {
                 ApplicationContext.Current.Services.MediaService.Save(MediaItem);
diff --git a/src/umbraco.cms/businesslogic/web/Document.cs b/src/umbraco.cms/businesslogic/web/Document.cs
index e45ea54da7..d9135fefea 100644
--- a/src/umbraco.cms/businesslogic/web/Document.cs
+++ b/src/umbraco.cms/businesslogic/web/Document.cs
@@ -936,6 +936,9 @@ namespace umbraco.cms.businesslogic.web
         [Obsolete("Obsolete, Use Umbraco.Core.Services.ContentService.Save()", false)]
         public override void Save()
         {
+            var e = new SaveEventArgs();
+            FireBeforeSave(e);
+
             foreach (var property in GenericProperties)
             {
                 if (property.Value == null)
@@ -943,9 +946,6 @@ namespace umbraco.cms.businesslogic.web
 
                 Content.SetValue(property.PropertyType.Alias, property.Value);
             }
-            
-            var e = new SaveEventArgs();
-            FireBeforeSave(e);
 
             if (!e.Cancel)
             {