diff --git a/src/Umbraco.Core/IO/MediaFileSystem.cs b/src/Umbraco.Core/IO/MediaFileSystem.cs
index b5955f825d..6e1d554c1f 100644
--- a/src/Umbraco.Core/IO/MediaFileSystem.cs
+++ b/src/Umbraco.Core/IO/MediaFileSystem.cs
@@ -341,36 +341,35 @@ namespace Umbraco.Core.IO
 
         // fixme - what's below belongs to the upload property editor, not the media filesystem!
 
-        public void SetUploadFile(IContentBase content, string propertyTypeAlias, string filename, Stream filestream)
+        public void SetUploadFile(IContentBase content, string propertyTypeAlias, string filename, Stream filestream, int? languageId = null, string segment = null)
         {
             var property = GetProperty(content, propertyTypeAlias);
-            var svalue = property.GetValue() as string;
-            var oldpath = svalue == null ? null : GetRelativePath(svalue);
+            var oldpath = property.GetValue(languageId, segment) is string svalue ? GetRelativePath(svalue) : null;
             var filepath = StoreFile(content, property.PropertyType, filename, filestream, oldpath);
-            property.SetValue(GetUrl(filepath));
-            SetUploadFile(content, property, filepath, filestream);
+            property.SetValue(GetUrl(filepath), languageId, segment);
+            SetUploadFile(content, property, filepath, filestream, languageId, segment);
         }
 
-        public void SetUploadFile(IContentBase content, string propertyTypeAlias, string filepath)
+        public void SetUploadFile(IContentBase content, string propertyTypeAlias, string filepath, int? languageId = null, string segment = null)
         {
             var property = GetProperty(content, propertyTypeAlias);
-            var svalue = property.GetValue() as string;
-            var oldpath = svalue == null ? null : GetRelativePath(svalue); // FIXME DELETE?
+            // fixme delete?
+            var oldpath = property.GetValue(languageId, segment) is string svalue ? GetRelativePath(svalue) : null;
             if (string.IsNullOrWhiteSpace(oldpath) == false && oldpath != filepath)
                 DeleteFile(oldpath);
-            property.SetValue(GetUrl(filepath));
+            property.SetValue(GetUrl(filepath), languageId, segment);
             using (var filestream = OpenFile(filepath))
             {
-                SetUploadFile(content, property, filepath, filestream);
+                SetUploadFile(content, property, filepath, filestream, languageId, segment);
             }
         }
 
         // sets a file for the FileUpload property editor
         // ie generates thumbnails and populates autofill properties
-        private void SetUploadFile(IContentBase content, Property property, string filepath, Stream filestream)
+        private void SetUploadFile(IContentBase content, Property property, string filepath, Stream filestream, int? languageId = null, string segment = null)
         {
             // will use filepath for extension, and filestream for length
-            UploadAutoFillProperties.Populate(content, property.Alias, filepath, filestream);
+            UploadAutoFillProperties.Populate(content, property.Alias, filepath, filestream, languageId, segment);
         }
 
         #endregion
diff --git a/src/Umbraco.Core/Media/UploadAutoFillProperties.cs b/src/Umbraco.Core/Media/UploadAutoFillProperties.cs
index 2639024cb0..3fdaf7b3d3 100644
--- a/src/Umbraco.Core/Media/UploadAutoFillProperties.cs
+++ b/src/Umbraco.Core/Media/UploadAutoFillProperties.cs
@@ -41,7 +41,9 @@ namespace Umbraco.Core.Media
         /// </summary>
         /// <param name="content">The content item.</param>
         /// <param name="propertyTypeAlias">The property type alias.</param>
-        public void Reset(IContentBase content, string propertyTypeAlias)
+        /// <param name="languageId">Variation language.</param>
+        /// <param name="segment">Variation segment.</param>
+        public void Reset(IContentBase content, string propertyTypeAlias, int? languageId, string segment)
         {
             if (content == null) throw new ArgumentNullException(nameof(content));
             if (propertyTypeAlias == null) throw new ArgumentNullException(nameof(propertyTypeAlias));
@@ -51,7 +53,7 @@ namespace Umbraco.Core.Media
             if (autoFillConfig == null) return; // nothing
 
             // reset
-            Reset(content, autoFillConfig);
+            Reset(content, autoFillConfig, languageId, segment);
         }
 
         /// <summary>
@@ -59,12 +61,14 @@ namespace Umbraco.Core.Media
         /// </summary>
         /// <param name="content">The content item.</param>
         /// <param name="autoFillConfig">The auto-fill configuration.</param>
-        public void Reset(IContentBase content, IImagingAutoFillUploadField autoFillConfig)
+        /// <param name="languageId">Variation language.</param>
+        /// <param name="segment">Variation segment.</param>
+        public void Reset(IContentBase content, IImagingAutoFillUploadField autoFillConfig, int? languageId, string segment)
         {
             if (content == null) throw new ArgumentNullException(nameof(content));
             if (autoFillConfig == null) throw new ArgumentNullException(nameof(autoFillConfig));
 
-            ResetProperties(content, autoFillConfig);
+            ResetProperties(content, autoFillConfig, languageId, segment);
         }
 
         /// <summary>
@@ -73,7 +77,9 @@ namespace Umbraco.Core.Media
         /// <param name="content">The content item.</param>
         /// <param name="propertyTypeAlias">The property type alias.</param>
         /// <param name="filepath">The filesystem-relative filepath, or null to clear properties.</param>
-        public void Populate(IContentBase content, string propertyTypeAlias, string filepath)
+        /// <param name="languageId">Variation language.</param>
+        /// <param name="segment">Variation segment.</param>
+        public void Populate(IContentBase content, string propertyTypeAlias, string filepath, int? languageId, string segment)
         {
             if (content == null) throw new ArgumentNullException(nameof(content));
             if (propertyTypeAlias == null) throw new ArgumentNullException(nameof(propertyTypeAlias));
@@ -86,7 +92,7 @@ namespace Umbraco.Core.Media
             if (autoFillConfig == null) return; // nothing
 
             // populate
-            Populate(content, autoFillConfig, filepath);
+            Populate(content, autoFillConfig, filepath, languageId, segment);
         }
 
         /// <summary>
@@ -96,7 +102,9 @@ namespace Umbraco.Core.Media
         /// <param name="propertyTypeAlias">The property type alias.</param>
         /// <param name="filepath">The filesystem-relative filepath, or null to clear properties.</param>
         /// <param name="filestream">The stream containing the file data.</param>
-        public void Populate(IContentBase content, string propertyTypeAlias, string filepath, Stream filestream)
+        /// <param name="languageId">Variation language.</param>
+        /// <param name="segment">Variation segment.</param>
+        public void Populate(IContentBase content, string propertyTypeAlias, string filepath, Stream filestream, int? languageId, string segment)
         {
             if (content == null) throw new ArgumentNullException(nameof(content));
             if (propertyTypeAlias == null) throw new ArgumentNullException(nameof(propertyTypeAlias));
@@ -109,7 +117,7 @@ namespace Umbraco.Core.Media
             if (autoFillConfig == null) return; // nothing
 
             // populate
-            Populate(content, autoFillConfig, filepath, filestream);
+            Populate(content, autoFillConfig, filepath, filestream, languageId, segment);
         }
 
         /// <summary>
@@ -119,7 +127,9 @@ namespace Umbraco.Core.Media
         /// <param name="autoFillConfig">The auto-fill configuration.</param>
         /// <param name="filepath">The filesystem path to the uploaded file.</param>
         /// <remarks>The <paramref name="filepath"/> parameter is the path relative to the filesystem.</remarks>
-        public void Populate(IContentBase content, IImagingAutoFillUploadField autoFillConfig, string filepath)
+        /// <param name="languageId">Variation language.</param>
+        /// <param name="segment">Variation segment.</param>
+        public void Populate(IContentBase content, IImagingAutoFillUploadField autoFillConfig, string filepath, int? languageId, string segment)
         {
             if (content == null) throw new ArgumentNullException(nameof(content));
             if (autoFillConfig == null) throw new ArgumentNullException(nameof(autoFillConfig));
@@ -127,7 +137,7 @@ namespace Umbraco.Core.Media
             // no file = reset, file = auto-fill
             if (filepath.IsNullOrWhiteSpace())
             {
-                ResetProperties(content, autoFillConfig);
+                ResetProperties(content, autoFillConfig, languageId, segment);
             }
             else
             {
@@ -138,13 +148,13 @@ namespace Umbraco.Core.Media
                     {
                         var extension = (Path.GetExtension(filepath) ?? "").TrimStart('.');
                         var size = _mediaFileSystem.IsImageFile(extension) ? (Size?) _mediaFileSystem.GetDimensions(filestream) : null;
-                        SetProperties(content, autoFillConfig, size, filestream.Length, extension);
+                        SetProperties(content, autoFillConfig, size, filestream.Length, extension, languageId, segment);
                     }
                 }
                 catch (Exception ex)
                 {
                     _logger.Error(typeof(UploadAutoFillProperties), $"Could not populate upload auto-fill properties for file \"{filepath}\".", ex);
-                    ResetProperties(content, autoFillConfig);
+                    ResetProperties(content, autoFillConfig, languageId, segment);
                 }
             }
         }
@@ -156,7 +166,9 @@ namespace Umbraco.Core.Media
         /// <param name="autoFillConfig"></param>
         /// <param name="filepath">The filesystem-relative filepath, or null to clear properties.</param>
         /// <param name="filestream">The stream containing the file data.</param>
-        public void Populate(IContentBase content, IImagingAutoFillUploadField autoFillConfig, string filepath, Stream filestream)
+        /// <param name="languageId">Variation language.</param>
+        /// <param name="segment">Variation segment.</param>
+        public void Populate(IContentBase content, IImagingAutoFillUploadField autoFillConfig, string filepath, Stream filestream, int? languageId, string segment)
         {
             if (content == null) throw new ArgumentNullException(nameof(content));
             if (autoFillConfig == null) throw new ArgumentNullException(nameof(autoFillConfig));
@@ -164,50 +176,50 @@ namespace Umbraco.Core.Media
             // no file = reset, file = auto-fill
             if (filepath.IsNullOrWhiteSpace() || filestream == null)
             {
-                ResetProperties(content, autoFillConfig);
+                ResetProperties(content, autoFillConfig, languageId, segment);
             }
             else
             {
                 var extension = (Path.GetExtension(filepath) ?? "").TrimStart('.');
                 var size = _mediaFileSystem.IsImageFile(extension) ? (Size?)_mediaFileSystem.GetDimensions(filestream) : null;
-                SetProperties(content, autoFillConfig, size, filestream.Length, extension);
+                SetProperties(content, autoFillConfig, size, filestream.Length, extension, languageId, segment);
             }
         }
 
-        private static void SetProperties(IContentBase content, IImagingAutoFillUploadField autoFillConfig, Size? size, long length, string extension)
+        private static void SetProperties(IContentBase content, IImagingAutoFillUploadField autoFillConfig, Size? size, long length, string extension, int? languageId, string segment)
         {
             if (content == null) throw new ArgumentNullException(nameof(content));
             if (autoFillConfig == null) throw new ArgumentNullException(nameof(autoFillConfig));
 
             if (content.Properties.Contains(autoFillConfig.WidthFieldAlias))
-                content.Properties[autoFillConfig.WidthFieldAlias].SetValue(size.HasValue ? size.Value.Width.ToInvariantString() : string.Empty);
+                content.Properties[autoFillConfig.WidthFieldAlias].SetValue(size.HasValue ? size.Value.Width.ToInvariantString() : string.Empty, languageId, segment);
 
             if (content.Properties.Contains(autoFillConfig.HeightFieldAlias))
-                content.Properties[autoFillConfig.HeightFieldAlias].SetValue(size.HasValue ? size.Value.Height.ToInvariantString() : string.Empty);
+                content.Properties[autoFillConfig.HeightFieldAlias].SetValue(size.HasValue ? size.Value.Height.ToInvariantString() : string.Empty, languageId, segment);
 
             if (content.Properties.Contains(autoFillConfig.LengthFieldAlias))
-                content.Properties[autoFillConfig.LengthFieldAlias].SetValue(length);
+                content.Properties[autoFillConfig.LengthFieldAlias].SetValue(length, languageId, segment);
 
             if (content.Properties.Contains(autoFillConfig.ExtensionFieldAlias))
-                content.Properties[autoFillConfig.ExtensionFieldAlias].SetValue(extension);
+                content.Properties[autoFillConfig.ExtensionFieldAlias].SetValue(extension, languageId, segment);
         }
 
-        private static void ResetProperties(IContentBase content, IImagingAutoFillUploadField autoFillConfig)
+        private static void ResetProperties(IContentBase content, IImagingAutoFillUploadField autoFillConfig, int? languageId, string segment)
         {
             if (content == null) throw new ArgumentNullException(nameof(content));
             if (autoFillConfig == null) throw new ArgumentNullException(nameof(autoFillConfig));
 
             if (content.Properties.Contains(autoFillConfig.WidthFieldAlias))
-                content.Properties[autoFillConfig.WidthFieldAlias].SetValue(string.Empty);
+                content.Properties[autoFillConfig.WidthFieldAlias].SetValue(string.Empty, languageId, segment);
 
             if (content.Properties.Contains(autoFillConfig.HeightFieldAlias))
-                content.Properties[autoFillConfig.HeightFieldAlias].SetValue(string.Empty);
+                content.Properties[autoFillConfig.HeightFieldAlias].SetValue(string.Empty, languageId, segment);
 
             if (content.Properties.Contains(autoFillConfig.LengthFieldAlias))
-                content.Properties[autoFillConfig.LengthFieldAlias].SetValue(string.Empty);
+                content.Properties[autoFillConfig.LengthFieldAlias].SetValue(string.Empty, languageId, segment);
 
             if (content.Properties.Contains(autoFillConfig.ExtensionFieldAlias))
-                content.Properties[autoFillConfig.ExtensionFieldAlias].SetValue(string.Empty);
+                content.Properties[autoFillConfig.ExtensionFieldAlias].SetValue(string.Empty, languageId, segment);
         }
     }
 }
diff --git a/src/Umbraco.Core/Models/ContentBase.cs b/src/Umbraco.Core/Models/ContentBase.cs
index 1d728ede8b..6adec3db5f 100644
--- a/src/Umbraco.Core/Models/ContentBase.cs
+++ b/src/Umbraco.Core/Models/ContentBase.cs
@@ -293,28 +293,24 @@ namespace Umbraco.Core.Models
             Properties.Add(property);
         }
 
-        // fixme - these three use an extension method that needs to be adapted too
-
         // HttpPostedFileBase is the base class that can be mocked
         // HttpPostedFile is what we get in ASP.NET
         // HttpPostedFileWrapper wraps sealed HttpPostedFile as HttpPostedFileBase
 
         /// <summary>
-        /// Sets the posted file value of a Property
+        /// Sets the posted file value of a property.
         /// </summary>
-        public virtual void SetValue(string propertyTypeAlias, HttpPostedFile value)
+        public virtual void SetValue(string propertyTypeAlias, HttpPostedFile value, int? languageId = null, string segment = null)
         {
-            ContentExtensions.SetValue(this, propertyTypeAlias, new HttpPostedFileWrapper(value));
+            ContentExtensions.SetValue(this, propertyTypeAlias, new HttpPostedFileWrapper(value), languageId, segment);
         }
 
         /// <summary>
-        /// Sets the posted file base value of a Property
+        /// Sets the posted file value of a property.
         /// </summary>
-        /// <param name="propertyTypeAlias">Alias of the PropertyType</param>
-        /// <param name="value">Value to set for the Property</param>
-        public virtual void SetValue(string propertyTypeAlias, HttpPostedFileBase value)
+        public virtual void SetValue(string propertyTypeAlias, HttpPostedFileBase value, int? languageId = null, string segment = null)
         {
-            ContentExtensions.SetValue(this, propertyTypeAlias, value);
+            ContentExtensions.SetValue(this, propertyTypeAlias, value, languageId, segment);
         }
 
         #endregion
diff --git a/src/Umbraco.Core/Models/ContentExtensions.cs b/src/Umbraco.Core/Models/ContentExtensions.cs
index 21d6b9b80f..e34d7026da 100644
--- a/src/Umbraco.Core/Models/ContentExtensions.cs
+++ b/src/Umbraco.Core/Models/ContentExtensions.cs
@@ -267,12 +267,9 @@ namespace Umbraco.Core.Models
         #region SetValue for setting file contents
 
         /// <summary>
-        /// Stores and sets an uploaded HttpPostedFileBase as a property value.
+        /// Sets the posted file value of a property.
         /// </summary>
-        /// <param name="content"><see cref="IContentBase"/>A content item.</param>
-        /// <param name="propertyTypeAlias">The property alias.</param>
-        /// <param name="value">The uploaded <see cref="HttpPostedFileBase"/>.</param>
-        public static void SetValue(this IContentBase content, string propertyTypeAlias, HttpPostedFileBase value)
+        public static void SetValue(this IContentBase content, string propertyTypeAlias, HttpPostedFileBase value, int? languageId = null, string segment = null)
         {
             // ensure we get the filename without the path in IE in intranet mode
             // http://stackoverflow.com/questions/382464/httppostedfile-filename-different-from-ie
@@ -291,20 +288,16 @@ namespace Umbraco.Core.Models
             if (string.IsNullOrWhiteSpace(filename)) return;
             filename = filename.ToLower(); // fixme - er... why?
 
-            MediaFileSystem.SetUploadFile(content, propertyTypeAlias, filename, value.InputStream);
+            MediaFileSystem.SetUploadFile(content, propertyTypeAlias, filename, value.InputStream, languageId, segment);
         }
 
         /// <summary>
-        /// Stores and sets a file as a property value.
+        /// Sets the posted file value of a property.
         /// </summary>
-        /// <param name="content"><see cref="IContentBase"/>A content item.</param>
-        /// <param name="propertyTypeAlias">The property alias.</param>
-        /// <param name="filename">The name of the file.</param>
-        /// <param name="filestream">A stream containing the file data.</param>
         /// <remarks>This really is for FileUpload fields only, and should be obsoleted. For anything else,
         /// you need to store the file by yourself using Store and then figure out
         /// how to deal with auto-fill properties (if any) and thumbnails (if any) by yourself.</remarks>
-        public static void SetValue(this IContentBase content, string propertyTypeAlias, string filename, Stream filestream)
+        public static void SetValue(this IContentBase content, string propertyTypeAlias, string filename, Stream filestream, int? languageId = null, string segment = null)
         {
             if (filename == null || filestream == null) return;
 
@@ -313,7 +306,7 @@ namespace Umbraco.Core.Models
             if (string.IsNullOrWhiteSpace(filename)) return;
             filename = filename.ToLower(); // fixme - er... why?
 
-            MediaFileSystem.SetUploadFile(content, propertyTypeAlias, filename, filestream);
+            MediaFileSystem.SetUploadFile(content, propertyTypeAlias, filename, filestream, languageId, segment);
         }
 
         /// <summary>
diff --git a/src/Umbraco.Web/PropertyEditors/FileUploadPropertyEditor.cs b/src/Umbraco.Web/PropertyEditors/FileUploadPropertyEditor.cs
index 8a36ee34b5..79824c96d7 100644
--- a/src/Umbraco.Web/PropertyEditors/FileUploadPropertyEditor.cs
+++ b/src/Umbraco.Web/PropertyEditors/FileUploadPropertyEditor.cs
@@ -148,7 +148,6 @@ namespace Umbraco.Web.PropertyEditors
         /// <summary>
         /// Auto-fill properties (or clear).
         /// </summary>
-        /// <param name="model">The content.</param>
         private void AutoFillProperties(IContentBase model)
         {
             var properties = model.Properties.Where(x => IsUploadField(x, false));
@@ -158,11 +157,14 @@ namespace Umbraco.Web.PropertyEditors
                 var autoFillConfig = _mediaFileSystem.UploadAutoFillProperties.GetConfig(property.Alias);
                 if (autoFillConfig == null) continue;
 
-                var svalue = property.GetValue() as string;
-                if (string.IsNullOrWhiteSpace(svalue))
-                    _mediaFileSystem.UploadAutoFillProperties.Reset(model, autoFillConfig);
-                else
-                    _mediaFileSystem.UploadAutoFillProperties.Populate(model, autoFillConfig, _mediaFileSystem.GetRelativePath(svalue));
+                foreach (var pvalue in property.Values)
+                {
+                    var svalue = property.GetValue(pvalue.LanguageId, pvalue.Segment) as string;
+                    if (string.IsNullOrWhiteSpace(svalue))
+                        _mediaFileSystem.UploadAutoFillProperties.Reset(model, autoFillConfig, pvalue.LanguageId, pvalue.Segment);
+                    else
+                        _mediaFileSystem.UploadAutoFillProperties.Populate(model, autoFillConfig, _mediaFileSystem.GetRelativePath(svalue), pvalue.LanguageId, pvalue.Segment);
+                }
             }
         }
 
@@ -232,22 +234,20 @@ namespace Umbraco.Web.PropertyEditors
             {
                 public IEnumerable<ValidationResult> Validate(object value, PreValueCollection preValues, PropertyEditor editor)
                 {
-                    var json = value as JArray;
-                    if (json == null) yield break;
+                    if (!(value is JArray json)) yield break;
 
                     //validate each item which is a json object
                     for (var index = 0; index < json.Count; index++)
                     {
                         var i = json[index];
                         var jItem = i as JObject;
-                        if (jItem == null || jItem["value"] == null) continue;
+                        if (jItem?["value"] == null) continue;
 
                         //NOTE: we will be removing empty values when persisting so no need to validate
                         var asString = jItem["value"].ToString();
                         if (asString.IsNullOrWhiteSpace()) continue;
 
-                        int parsed;
-                        if (int.TryParse(asString, out parsed) == false)
+                        if (int.TryParse(asString, out _) == false)
                         {
                             yield return new ValidationResult("The value " + asString + " is not a valid number", new[]
                             {
diff --git a/src/Umbraco.Web/PropertyEditors/ImageCropperPropertyEditor.cs b/src/Umbraco.Web/PropertyEditors/ImageCropperPropertyEditor.cs
index ab1db28fe8..167e3d2a0b 100644
--- a/src/Umbraco.Web/PropertyEditors/ImageCropperPropertyEditor.cs
+++ b/src/Umbraco.Web/PropertyEditors/ImageCropperPropertyEditor.cs
@@ -18,7 +18,6 @@ namespace Umbraco.Web.PropertyEditors
     public class ImageCropperPropertyEditor : PropertyEditor
     {
         private readonly MediaFileSystem _mediaFileSystem;
-        private readonly IContentSection _contentSettings;
         private readonly IDataTypeService _dataTypeService;
         private readonly UploadAutoFillProperties _autoFillProperties;
         private IDictionary<string, object> _internalPreValues; // preValues
@@ -29,13 +28,9 @@ namespace Umbraco.Web.PropertyEditors
         public ImageCropperPropertyEditor(ILogger logger, MediaFileSystem mediaFileSystem, IContentSection contentSettings, IDataTypeService dataTypeService)
             : base(logger)
         {
-            if (mediaFileSystem == null) throw new ArgumentNullException(nameof(mediaFileSystem));
-            if (contentSettings == null) throw new ArgumentNullException(nameof(contentSettings));
-            if (dataTypeService == null) throw new ArgumentNullException(nameof(dataTypeService));
-
-            _mediaFileSystem = mediaFileSystem;
-            _contentSettings = contentSettings;
-            _dataTypeService = dataTypeService;
+            _mediaFileSystem = mediaFileSystem ?? throw new ArgumentNullException(nameof(mediaFileSystem));
+            var contentSettings1 = contentSettings ?? throw new ArgumentNullException(nameof(contentSettings));
+            _dataTypeService = dataTypeService ?? throw new ArgumentNullException(nameof(dataTypeService));
 
             _internalPreValues = new Dictionary<string, object>
                 {
@@ -43,13 +38,13 @@ namespace Umbraco.Web.PropertyEditors
                     {"src", ""}
                 };
 
-            _autoFillProperties = new UploadAutoFillProperties(_mediaFileSystem, Logger, _contentSettings);
+            _autoFillProperties = new UploadAutoFillProperties(_mediaFileSystem, Logger, contentSettings1);
         }
 
         public override IDictionary<string, object> DefaultPreValues
         {
-            get { return _internalPreValues; }
-            set { _internalPreValues = value; }
+            get => _internalPreValues;
+            set => _internalPreValues = value;
         }
 
         /// <summary>
@@ -157,9 +152,8 @@ namespace Umbraco.Web.PropertyEditors
             foreach (var property in properties)
             {
                 var jo = GetJObject((string) property.GetValue(), true);
-                if (jo == null || jo["src"] == null) continue;
 
-                var src = jo["src"].Value<string>();
+                var src = jo?["src"]?.Value<string>();
                 if (string.IsNullOrWhiteSpace(src)) continue;
 
                 var sourcePath = _mediaFileSystem.GetRelativePath(src);
@@ -208,7 +202,6 @@ namespace Umbraco.Web.PropertyEditors
         /// <summary>
         /// Auto-fill properties (or clear).
         /// </summary>
-        /// <param name="model">The content.</param>
         private void AutoFillProperties(IContentBase model)
         {
             var properties = model.Properties.Where(x => IsCropperField(x, false));
@@ -218,37 +211,40 @@ namespace Umbraco.Web.PropertyEditors
                 var autoFillConfig = _autoFillProperties.GetConfig(property.Alias);
                 if (autoFillConfig == null) continue;
 
-                var svalue = property.GetValue() as string;
-                if (string.IsNullOrWhiteSpace(svalue))
+                foreach (var pvalue in property.Values)
                 {
-                    _autoFillProperties.Reset(model, autoFillConfig);
-                    continue;
-                }
+                    var svalue = property.GetValue(pvalue.LanguageId, pvalue.Segment) as string;
+                    if (string.IsNullOrWhiteSpace(svalue))
+                    {
+                        _autoFillProperties.Reset(model, autoFillConfig, pvalue.LanguageId, pvalue.Segment);
+                        continue;
+                    }
 
-                var jo = GetJObject(svalue, false);
-                string src;
-                if (jo == null)
-                {
-                    // so we have a non-empty string value that cannot be parsed into a json object
-                    // see http://issues.umbraco.org/issue/U4-4756
-                    // it can happen when an image is uploaded via the folder browser, in which case
-                    // the property value will be the file source eg '/media/23454/hello.jpg' and we
-                    // are fixing that anomaly here - does not make any sense at all but... bah...
-                    var config = _dataTypeService
-                        .GetPreValuesByDataTypeId(property.PropertyType.DataTypeDefinitionId).FirstOrDefault();
-                    var crops = string.IsNullOrWhiteSpace(config) ? "[]" : config;
-                    src = svalue;
-                    property.SetValue("{\"src\": \"" + svalue + "\", \"crops\": " + crops + "}");
-                }
-                else
-                {
-                    src = jo["src"]?.Value<string>();
-                }
+                    var jo = GetJObject(svalue, false);
+                    string src;
+                    if (jo == null)
+                    {
+                        // so we have a non-empty string value that cannot be parsed into a json object
+                        // see http://issues.umbraco.org/issue/U4-4756
+                        // it can happen when an image is uploaded via the folder browser, in which case
+                        // the property value will be the file source eg '/media/23454/hello.jpg' and we
+                        // are fixing that anomaly here - does not make any sense at all but... bah...
+                        var config = _dataTypeService
+                            .GetPreValuesByDataTypeId(property.PropertyType.DataTypeDefinitionId).FirstOrDefault();
+                        var crops = string.IsNullOrWhiteSpace(config) ? "[]" : config;
+                        src = svalue;
+                        property.SetValue("{\"src\": \"" + svalue + "\", \"crops\": " + crops + "}");
+                    }
+                    else
+                    {
+                        src = jo["src"]?.Value<string>();
+                    }
 
-                if (src == null)
-                    _autoFillProperties.Reset(model, autoFillConfig);
-                else
-                    _autoFillProperties.Populate(model, autoFillConfig, _mediaFileSystem.GetRelativePath(src));
+                    if (src == null)
+                        _autoFillProperties.Reset(model, autoFillConfig, pvalue.LanguageId, pvalue.Segment);
+                    else
+                        _autoFillProperties.Populate(model, autoFillConfig, _mediaFileSystem.GetRelativePath(src), pvalue.LanguageId, pvalue.Segment);
+                }
             }
         }