diff --git a/src/Umbraco.Core/Models/ContentExtensions.cs b/src/Umbraco.Core/Models/ContentExtensions.cs
index 9f83eaca5c..c76377dc6e 100644
--- a/src/Umbraco.Core/Models/ContentExtensions.cs
+++ b/src/Umbraco.Core/Models/ContentExtensions.cs
@@ -1,6 +1,14 @@
 using System;
+using System.Drawing;
+using System.Drawing.Drawing2D;
+using System.Drawing.Imaging;
+using System.IO;
 using System.Linq;
+using System.Web;
+using System.Xml;
 using System.Xml.Linq;
+using Umbraco.Core.Configuration;
+using Umbraco.Core.IO;
 using Umbraco.Core.Models.Membership;
 using Umbraco.Core.Persistence;
 using Umbraco.Core.Persistence.UnitOfWork;
@@ -45,6 +53,283 @@ namespace Umbraco.Core.Models
             }
         }
 
+        /// <summary>
+        /// Sets and uploads the file from a HttpPostedFileBase object as the property value
+        /// </summary>
+        /// <param name="media"><see cref="IMedia"/> to add property value to</param>
+        /// <param name="propertyTypeAlias">Alias of the property to save the value on</param>
+        /// <param name="value">The <see cref="HttpPostedFileBase"/> containing the file that will be uploaded</param>
+        public static void SetValue(this IMedia media, string propertyTypeAlias, HttpPostedFileBase value)
+        {
+            var name =
+                IOHelper.SafeFileName(
+                    value.FileName.Substring(value.FileName.LastIndexOf(IOHelper.DirSepChar) + 1,
+                                             value.FileName.Length - value.FileName.LastIndexOf(IOHelper.DirSepChar) - 1)
+                         .ToLower());
+
+            if(string.IsNullOrEmpty(name) == false)
+                SetFileOnContent(media, propertyTypeAlias, name, value.InputStream);
+        }
+
+        /// <summary>
+        /// Sets and uploads the file from a HttpPostedFile object as the property value
+        /// </summary>
+        /// <param name="media"><see cref="IMedia"/> to add property value to</param>
+        /// <param name="propertyTypeAlias">Alias of the property to save the value on</param>
+        /// <param name="value">The <see cref="HttpPostedFile"/> containing the file that will be uploaded</param>
+        public static void SetValue(this IMedia media, string propertyTypeAlias, HttpPostedFile value)
+        {
+            var name =
+                IOHelper.SafeFileName(
+                    value.FileName.Substring(value.FileName.LastIndexOf(IOHelper.DirSepChar) + 1,
+                                            value.FileName.Length - value.FileName.LastIndexOf(IOHelper.DirSepChar) - 1)
+                        .ToLower());
+
+            if (string.IsNullOrEmpty(name) == false)
+                SetFileOnContent(media, propertyTypeAlias, name, value.InputStream);
+        }
+
+        /// <summary>
+        /// Sets and uploads the file from a HttpPostedFileWrapper object as the property value
+        /// </summary>
+        /// <param name="media"><see cref="IMedia"/> to add property value to</param>
+        /// <param name="propertyTypeAlias">Alias of the property to save the value on</param>
+        /// <param name="value">The <see cref="HttpPostedFileWrapper"/> containing the file that will be uploaded</param>
+        public static void SetValue(this IMedia media, string propertyTypeAlias, HttpPostedFileWrapper value)
+        {
+            if (string.IsNullOrEmpty(value.FileName) == false)
+                SetFileOnContent(media, propertyTypeAlias, value.FileName, value.InputStream);
+        }
+
+        /// <summary>
+        /// Sets and uploads the file from a HttpPostedFileBase object as the property value
+        /// </summary>
+        /// <param name="content"><see cref="IContent"/> to add property value to</param>
+        /// <param name="propertyTypeAlias">Alias of the property to save the value on</param>
+        /// <param name="value">The <see cref="HttpPostedFileBase"/> containing the file that will be uploaded</param>
+        public static void SetValue(this IContent content, string propertyTypeAlias, HttpPostedFileBase value)
+        {
+            var name =
+                IOHelper.SafeFileName(
+                    value.FileName.Substring(value.FileName.LastIndexOf(IOHelper.DirSepChar) + 1,
+                                             value.FileName.Length - value.FileName.LastIndexOf(IOHelper.DirSepChar) - 1)
+                         .ToLower());
+
+            if (string.IsNullOrEmpty(name) == false)
+                SetFileOnContent(content, propertyTypeAlias, name, value.InputStream);
+        }
+
+        /// <summary>
+        /// Sets and uploads the file from a HttpPostedFile object as the property value
+        /// </summary>
+        /// <param name="content"><see cref="IContent"/> to add property value to</param>
+        /// <param name="propertyTypeAlias">Alias of the property to save the value on</param>
+        /// <param name="value">The <see cref="HttpPostedFile"/> containing the file that will be uploaded</param>
+        public static void SetValue(this IContent content, string propertyTypeAlias, HttpPostedFile value)
+        {
+            var name =
+                IOHelper.SafeFileName(
+                    value.FileName.Substring(value.FileName.LastIndexOf(IOHelper.DirSepChar) + 1,
+                                            value.FileName.Length - value.FileName.LastIndexOf(IOHelper.DirSepChar) - 1)
+                        .ToLower());
+
+            if (string.IsNullOrEmpty(name) == false)
+                SetFileOnContent(content, propertyTypeAlias, name, value.InputStream);
+        }
+
+        /// <summary>
+        /// Sets and uploads the file from a HttpPostedFileWrapper object as the property value
+        /// </summary>
+        /// <param name="content"><see cref="IContent"/> to add property value to</param>
+        /// <param name="propertyTypeAlias">Alias of the property to save the value on</param>
+        /// <param name="value">The <see cref="HttpPostedFileWrapper"/> containing the file that will be uploaded</param>
+        public static void SetValue(this IContent content, string propertyTypeAlias, HttpPostedFileWrapper value)
+        {
+            if (string.IsNullOrEmpty(value.FileName) == false)
+                SetFileOnContent(content, propertyTypeAlias, value.FileName, value.InputStream);
+        }
+
+        private static void SetFileOnContent(IContentBase content, string propertyTypeAlias, string name, Stream fileStream)
+        {
+            var property = content.Properties.FirstOrDefault(x => x.Alias == propertyTypeAlias);
+            if(property == null)
+                return;
+
+            bool supportsResizing = false;
+            string fileName = UmbracoSettings.UploadAllowDirectories
+                                              ? Path.Combine(property.Id.ToString(), name)
+                                              : property.Id + "-" + name;
+            string extension = Path.GetExtension(name);
+
+            var fs = FileSystemProviderManager.Current.GetFileSystemProvider<MediaFileSystem>();
+            fs.AddFile(fileName, fileStream);
+
+            //Check if file supports resizing and create thumbnails
+            if (("," + UmbracoSettings.ImageFileTypes + ",").Contains(string.Format(",{0},", extension)))
+            {
+                supportsResizing = true;
+
+                // Make default thumbnail
+                var thumbUrl = Resize(fs, fileName, extension, 100, "thumb");
+
+                //Look up Prevalues for this upload datatype - if it is an upload datatype
+                var uploadFieldId = new Guid("5032a6e6-69e3-491d-bb28-cd31cd11086c");
+                if (property.PropertyType.DataTypeControlId == uploadFieldId)
+                {
+                    //Get Prevalues by the DataType's Id: property.PropertyType.DataTypeId
+                    //var definition = ApplicationContext.Current.Services.DataTypeService.GetDataTypeDefinitionById(property.PropertyType.DataTypeId);
+                }
+            }
+
+            //Check for auto fill of additional properties
+            if (UmbracoSettings.ImageAutoFillImageProperties != null)
+            {
+                XmlNode uploadFieldConfigNode =
+                    UmbracoSettings.ImageAutoFillImageProperties.SelectSingleNode(
+                        string.Format("uploadField [@alias = \"{0}\"]", propertyTypeAlias));
+                
+                if (uploadFieldConfigNode != null)
+                {
+                    // Only add dimensions to web images
+                    if (supportsResizing)
+                    {
+                        SetPropertyValue(content, uploadFieldConfigNode, "widthFieldAlias", GetDimensions(fs, fileName).Item1);
+                        SetPropertyValue(content, uploadFieldConfigNode, "heightFieldAlias", GetDimensions(fs, fileName).Item2);
+                    }
+                    else
+                    {
+                        SetPropertyValue(content, uploadFieldConfigNode, "widthFieldAlias", string.Empty);
+                        SetPropertyValue(content, uploadFieldConfigNode, "heightFieldAlias", string.Empty);
+                    }
+
+                    SetPropertyValue(content, uploadFieldConfigNode, "lengthFieldAlias", fs.GetSize(fileName));
+                    SetPropertyValue(content, uploadFieldConfigNode, "extensionFieldAlias", extension);
+                }
+            }
+
+            //Set the value of the property to that of the uploaded file's url
+            property.Value = fs.GetUrl(fileName);
+        }
+
+        private static void SetPropertyValue(IContentBase content, XmlNode uploadFieldConfigNode, string propertyAlias, object propertyValue)
+        {
+            XmlNode propertyNode = uploadFieldConfigNode.SelectSingleNode(propertyAlias);
+            if (propertyNode != null && string.IsNullOrEmpty(propertyNode.FirstChild.Value) == false)
+            {
+                content.SetValue(propertyNode.FirstChild.Value, propertyValue);
+            }
+        }
+        
+        private static string Resize(MediaFileSystem fileSystem, string path, string extension, int maxWidthHeight, string fileNameAddition)
+        {
+            var fileNameThumb = DoResize(fileSystem, path, extension, GetDimensions(fileSystem, path).Item1, GetDimensions(fileSystem, path).Item2, maxWidthHeight, fileNameAddition);
+
+            return fileSystem.GetUrl(fileNameThumb);
+        }
+
+        private static Tuple<int, int> GetDimensions(MediaFileSystem fileSystem, string path)
+        {
+            var fs = fileSystem.OpenFile(path);
+            var image = Image.FromStream(fs);
+            var fileWidth = image.Width;
+            var fileHeight = image.Height;
+            fs.Close();
+            image.Dispose();
+
+            return new Tuple<int, int>(fileWidth, fileHeight);
+        }
+
+        private static string DoResize(MediaFileSystem fileSystem, string path, string extension, int width, int height, int maxWidthHeight, string fileNameAddition)
+        {
+            var fs = fileSystem.OpenFile(path);
+            var image = Image.FromStream(fs);
+            fs.Close();
+
+            string fileNameThumb = String.IsNullOrEmpty(fileNameAddition) ?
+                string.Format("{0}_UMBRACOSYSTHUMBNAIL.jpg", path.Substring(0, path.LastIndexOf("."))) :
+                string.Format("{0}_{1}.jpg", path.Substring(0, path.LastIndexOf(".")), fileNameAddition);
+
+            var thumb = GenerateThumbnail(fileSystem,
+                image,
+                maxWidthHeight,
+                width,
+                height,
+                path,
+                extension,
+                fileNameThumb,
+                maxWidthHeight == 0);
+
+            fileNameThumb = thumb.Item3;
+
+            image.Dispose();
+
+            return fileNameThumb;
+        }
+
+        private static Tuple<int, int, string> GenerateThumbnail(MediaFileSystem fileSystem, Image image, int maxWidthHeight, int fileWidth,
+                                                int fileHeight, string fullFilePath, string extension,
+                                                string thumbnailFileName, bool useFixedDimensions)
+        {
+            // Generate thumbnail
+            float f = 1;
+            if (!useFixedDimensions)
+            {
+                var fx = (float)image.Size.Width / (float)maxWidthHeight;
+                var fy = (float)image.Size.Height / (float)maxWidthHeight;
+
+                // must fit in thumbnail size
+                f = Math.Max(fx, fy); //if (f < 1) f = 1;
+            }
+
+            var widthTh = (int)Math.Round((float)fileWidth / f); int heightTh = (int)Math.Round((float)fileHeight / f);
+
+            // fixes for empty width or height
+            if (widthTh == 0)
+                widthTh = 1;
+            if (heightTh == 0)
+                heightTh = 1;
+
+            // Create new image with best quality settings
+            var bp = new Bitmap(widthTh, heightTh);
+            var g = Graphics.FromImage(bp);
+            g.SmoothingMode = SmoothingMode.HighQuality;
+            g.InterpolationMode = InterpolationMode.HighQualityBicubic;
+            g.PixelOffsetMode = PixelOffsetMode.HighQuality;
+            g.CompositingQuality = CompositingQuality.HighQuality;
+
+            // Copy the old image to the new and resized
+            var rect = new Rectangle(0, 0, widthTh, heightTh);
+            g.DrawImage(image, rect, 0, 0, image.Width, image.Height, GraphicsUnit.Pixel);
+
+            // Copy metadata
+            var imageEncoders = ImageCodecInfo.GetImageEncoders();
+            ImageCodecInfo codec = null;
+            if (extension.ToLower() == "png" || extension.ToLower() == "gif")
+                codec = imageEncoders.Single(t => t.MimeType.Equals("image/png"));
+            else
+                codec = imageEncoders.Single(t => t.MimeType.Equals("image/jpeg"));
+
+
+            // Set compresion ratio to 90%
+            var ep = new EncoderParameters();
+            ep.Param[0] = new EncoderParameter(Encoder.Quality, 90L);
+
+            // Save the new image using the dimensions of the image
+            string newFileName = thumbnailFileName.Replace("UMBRACOSYSTHUMBNAIL",
+                                                           string.Format("{0}x{1}", widthTh, heightTh));
+            var ms = new MemoryStream();
+            bp.Save(ms, codec, ep);
+            ms.Seek(0, 0);
+
+            fileSystem.AddFile(newFileName, ms);
+
+            ms.Close();
+            bp.Dispose();
+            g.Dispose();
+
+            return new Tuple<int, int, string>(widthTh, heightTh, newFileName);
+        }
+
         /// <summary>
         /// Gets the <see cref="IProfile"/> for the Creator of this content.
         /// </summary>
diff --git a/src/Umbraco.Core/Umbraco.Core.csproj b/src/Umbraco.Core/Umbraco.Core.csproj
index 631d84345d..c016413e76 100644
--- a/src/Umbraco.Core/Umbraco.Core.csproj
+++ b/src/Umbraco.Core/Umbraco.Core.csproj
@@ -54,6 +54,7 @@
       <SpecificVersion>False</SpecificVersion>
       <HintPath>..\..\lib\SQLCE4\System.Data.SqlServerCe.Entity.dll</HintPath>
     </Reference>
+    <Reference Include="System.Drawing" />
     <Reference Include="System.Runtime.Caching" />
     <Reference Include="System.Runtime.Serialization" />
     <Reference Include="System.Transactions" />