diff --git a/src/Umbraco.Examine/MediaValueSetBuilder.cs b/src/Umbraco.Examine/MediaValueSetBuilder.cs
index 3e5b9865cc..03e7f4944b 100644
--- a/src/Umbraco.Examine/MediaValueSetBuilder.cs
+++ b/src/Umbraco.Examine/MediaValueSetBuilder.cs
@@ -4,6 +4,7 @@ using System.Collections.Generic;
 using System.Linq;
 using Newtonsoft.Json;
 using Umbraco.Core;
+using Umbraco.Core.Logging;
 using Umbraco.Core.Models;
 using Umbraco.Core.PropertyEditors;
 using Umbraco.Core.PropertyEditors.ValueConverters;
@@ -16,14 +17,16 @@ namespace Umbraco.Examine
     {
         private readonly UrlSegmentProviderCollection _urlSegmentProviders;
         private readonly IUserService _userService;
+        private readonly ILogger _logger;
 
         public MediaValueSetBuilder(PropertyEditorCollection propertyEditors,
             UrlSegmentProviderCollection urlSegmentProviders,
-            IUserService userService)
+            IUserService userService, ILogger logger)
             : base(propertyEditors, false)
         {
             _urlSegmentProviders = urlSegmentProviders;
             _userService = userService;
+            _logger = logger;
         }
 
         /// <inheritdoc />
@@ -40,7 +43,17 @@ namespace Umbraco.Examine
 
                 if (umbracoFileSource.DetectIsJson())
                 {
-                    var cropper = JsonConvert.DeserializeObject<ImageCropperValue>(m.GetValue<string>(Constants.Conventions.Media.File));
+                    ImageCropperValue cropper = null;
+                    try
+                    {
+                        cropper = JsonConvert.DeserializeObject<ImageCropperValue>(
+                            m.GetValue<string>(Constants.Conventions.Media.File));
+                    }
+                    catch (Exception ex)
+                    {
+                        _logger.Error<MediaValueSetBuilder>(ex, $"Could not Deserialize ImageCropperValue for item with key {m.Key} ");
+                    }
+
                     if (cropper != null)
                     {
                         umbracoFilePath = cropper.Src;
diff --git a/src/Umbraco.Tests/UmbracoExamine/IndexInitializer.cs b/src/Umbraco.Tests/UmbracoExamine/IndexInitializer.cs
index 6c65ae8345..1653de827d 100644
--- a/src/Umbraco.Tests/UmbracoExamine/IndexInitializer.cs
+++ b/src/Umbraco.Tests/UmbracoExamine/IndexInitializer.cs
@@ -45,7 +45,7 @@ namespace Umbraco.Tests.UmbracoExamine
 
         public static MediaIndexPopulator GetMediaIndexRebuilder(PropertyEditorCollection propertyEditors, IMediaService mediaService)
         {
-            var mediaValueSetBuilder = new MediaValueSetBuilder(propertyEditors, new UrlSegmentProviderCollection(new[] { new DefaultUrlSegmentProvider() }), GetMockUserService());
+            var mediaValueSetBuilder = new MediaValueSetBuilder(propertyEditors, new UrlSegmentProviderCollection(new[] { new DefaultUrlSegmentProvider() }), GetMockUserService(), GetMockLogger());
             var mediaIndexDataSource = new MediaIndexPopulator(null, mediaService, mediaValueSetBuilder);
             return mediaIndexDataSource;
         }
@@ -146,6 +146,11 @@ namespace Umbraco.Tests.UmbracoExamine
             return mediaTypeServiceMock.Object;
         }
 
+        public static IProfilingLogger GetMockLogger()
+        {
+            return new ProfilingLogger(Mock.Of<ILogger>(), Mock.Of<IProfiler>());
+        }
+
         public static UmbracoContentIndex GetUmbracoIndexer(
             IProfilingLogger profilingLogger,
             Directory luceneDir,
diff --git a/src/Umbraco.Web/Models/Mapping/EntityMapDefinition.cs b/src/Umbraco.Web/Models/Mapping/EntityMapDefinition.cs
index 424054cd6c..f2099f2554 100644
--- a/src/Umbraco.Web/Models/Mapping/EntityMapDefinition.cs
+++ b/src/Umbraco.Web/Models/Mapping/EntityMapDefinition.cs
@@ -177,9 +177,8 @@ namespace Umbraco.Web.Models.Mapping
 
             target.Name = source.Values.ContainsKey("nodeName") ? source.Values["nodeName"] : "[no name]";
 
-            if (source.Values.ContainsKey(UmbracoExamineIndex.UmbracoFileFieldName))
+            if (source.Values.TryGetValue(UmbracoExamineIndex.UmbracoFileFieldName, out var umbracoFile))
             {
-                var umbracoFile = source.Values[UmbracoExamineIndex.UmbracoFileFieldName];
                 if (umbracoFile != null)
                 {
                     target.Name = $"{target.Name} ({umbracoFile})";