diff --git a/src/Umbraco.Core/Persistence/Repositories/ContentRepository.cs b/src/Umbraco.Core/Persistence/Repositories/ContentRepository.cs
index b38b19a2d8..08c159481b 100644
--- a/src/Umbraco.Core/Persistence/Repositories/ContentRepository.cs
+++ b/src/Umbraco.Core/Persistence/Repositories/ContentRepository.cs
@@ -498,7 +498,7 @@ namespace Umbraco.Core.Persistence.Repositories
             {
                 if (property.PropertyType.PropertyEditorAlias == Constants.PropertyEditors.UploadFieldAlias && property.Value != null &&
                     string.IsNullOrEmpty(property.Value.ToString()) == false
-                    && fs.FileExists(IOHelper.MapPath(property.Value.ToString())))
+                    && fs.FileExists(fs.GetRelativePath(property.Value.ToString())))
                 {
                     var relativeFilePath = fs.GetRelativePath(property.Value.ToString());
                     var parentDirectory = System.IO.Path.GetDirectoryName(relativeFilePath);
diff --git a/src/Umbraco.Core/Persistence/Repositories/MemberRepository.cs b/src/Umbraco.Core/Persistence/Repositories/MemberRepository.cs
index 595fcb033d..2bbb3439ca 100644
--- a/src/Umbraco.Core/Persistence/Repositories/MemberRepository.cs
+++ b/src/Umbraco.Core/Persistence/Repositories/MemberRepository.cs
@@ -398,7 +398,7 @@ namespace Umbraco.Core.Persistence.Repositories
             {
                 if (property.PropertyType.PropertyEditorAlias == uploadFieldAlias &&
                     string.IsNullOrEmpty(property.Value.ToString()) == false
-                    && fs.FileExists(IOHelper.MapPath(property.Value.ToString())))
+                    && fs.FileExists(fs.GetRelativePath(property.Value.ToString())))
                 {
                     var relativeFilePath = fs.GetRelativePath(property.Value.ToString());
                     var parentDirectory = System.IO.Path.GetDirectoryName(relativeFilePath);
diff --git a/src/Umbraco.Web/PropertyEditors/FileUploadPropertyEditor.cs b/src/Umbraco.Web/PropertyEditors/FileUploadPropertyEditor.cs
index 4934a457d8..28da565b9e 100644
--- a/src/Umbraco.Web/PropertyEditors/FileUploadPropertyEditor.cs
+++ b/src/Umbraco.Web/PropertyEditors/FileUploadPropertyEditor.cs
@@ -71,7 +71,7 @@ namespace Umbraco.Web.PropertyEditors
                     && x.Value != null                                                   
                     && string.IsNullOrEmpty(x.Value.ToString()) == false))
                 {
-                    if (fs.FileExists(IOHelper.MapPath(property.Value.ToString())))
+                    if (fs.FileExists(fs.GetRelativePath(property.Value.ToString())))
                     {
                         var currentPath = fs.GetRelativePath(property.Value.ToString());
                         var propertyId = e.Copy.Properties.First(x => x.Alias == property.Alias).Id;
diff --git a/src/Umbraco.Web/PropertyEditors/ImageCropperPropertyEditor.cs b/src/Umbraco.Web/PropertyEditors/ImageCropperPropertyEditor.cs
index bb6aff2e95..468d039936 100644
--- a/src/Umbraco.Web/PropertyEditors/ImageCropperPropertyEditor.cs
+++ b/src/Umbraco.Web/PropertyEditors/ImageCropperPropertyEditor.cs
@@ -89,7 +89,7 @@ namespace Umbraco.Web.PropertyEditors
 
                     if (json["src"] != null && json["src"].ToString().IsNullOrWhiteSpace() == false)
                     {
-                        if (fs.FileExists(IOHelper.MapPath(json["src"].ToString())))
+                        if (fs.FileExists(fs.GetRelativePath(json["src"].ToString())))
                         {
                             var currentPath = fs.GetRelativePath(json["src"].ToString());
                             var propertyId = e.Copy.Properties.First(x => x.Alias == property.Alias).Id;