diff --git a/src/NzbDrone.Core.Test/Messaging/Commands/CommandEqualityComparerFixture.cs b/src/NzbDrone.Core.Test/Messaging/Commands/CommandEqualityComparerFixture.cs
index 8154c7a24..364e62a48 100644
--- a/src/NzbDrone.Core.Test/Messaging/Commands/CommandEqualityComparerFixture.cs
+++ b/src/NzbDrone.Core.Test/Messaging/Commands/CommandEqualityComparerFixture.cs
@@ -1,17 +1,29 @@
-using System.Collections.Generic;
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using FizzWare.NBuilder;
 using FluentAssertions;
 using NUnit.Framework;
+using NzbDrone.Common.Extensions;
 using NzbDrone.Core.Indexers;
 using NzbDrone.Core.IndexerSearch;
 using NzbDrone.Core.MediaFiles.Commands;
+using NzbDrone.Core.MediaFiles.EpisodeImport.Manual;
 using NzbDrone.Core.Messaging.Commands;
 using NzbDrone.Core.Update.Commands;
+using NzbDrone.Test.Common;
 
 namespace NzbDrone.Core.Test.Messaging.Commands
 {
     [TestFixture]
     public class CommandEqualityComparerFixture
     {
+        private string GivenRandomPath()
+        {
+            return Path.Combine(@"C:\Tesst\", Guid.NewGuid().ToString()).AsOsAgnostic();
+        }
+
         [Test]
         public void should_return_true_when_there_are_no_properties()
         {
@@ -107,5 +119,43 @@ namespace NzbDrone.Core.Test.Messaging.Commands
 
             CommandEqualityComparer.Instance.Equals(command1, command2).Should().BeFalse();
         }
+
+        [Test]
+        public void should_return_true_when_commands_list_for_non_primitive_type_match()
+        {
+            var files1 = Builder<ManualImportFile>.CreateListOfSize(2)
+                                                  .All()
+                                                  .With(m => m.Path = GivenRandomPath())
+                                                  .Build()
+                                                  .ToList();
+
+            var files2 = files1.JsonClone();
+
+            var command1 = new ManualImportCommand { Files = files1 };
+            var command2 = new ManualImportCommand { Files = files2 };
+
+            CommandEqualityComparer.Instance.Equals(command1, command2).Should().BeTrue();
+        }
+
+        [Test]
+        public void should_return_false_when_commands_list_for_non_primitive_type_dont_match()
+        {
+            var files1 = Builder<ManualImportFile>.CreateListOfSize(2)
+                                                  .All()
+                                                  .With(m => m.Path = GivenRandomPath())
+                                                  .Build()
+                                                  .ToList();
+
+            var files2 = Builder<ManualImportFile>.CreateListOfSize(2)
+                                                  .All()
+                                                  .With(m => m.Path = GivenRandomPath())
+                                                  .Build()
+                                                  .ToList();
+
+            var command1 = new ManualImportCommand { Files = files1 };
+            var command2 = new ManualImportCommand { Files = files2 };
+
+            CommandEqualityComparer.Instance.Equals(command1, command2).Should().BeFalse();
+        }
     }
 }
diff --git a/src/NzbDrone.Core/MediaFiles/EpisodeImport/Manual/ManualImportFile.cs b/src/NzbDrone.Core/MediaFiles/EpisodeImport/Manual/ManualImportFile.cs
index f0d42b21d..318b7ff7d 100644
--- a/src/NzbDrone.Core/MediaFiles/EpisodeImport/Manual/ManualImportFile.cs
+++ b/src/NzbDrone.Core/MediaFiles/EpisodeImport/Manual/ManualImportFile.cs
@@ -1,9 +1,11 @@
-using System.Collections.Generic;
+using System;
+using System.Collections.Generic;
+using NzbDrone.Common.Extensions;
 using NzbDrone.Core.Qualities;
 
 namespace NzbDrone.Core.MediaFiles.EpisodeImport.Manual
 {
-    public class ManualImportFile
+    public class ManualImportFile : IEquatable<ManualImportFile>
     {
         public string Path { get; set; }
         public string FolderName { get; set; }
@@ -11,5 +13,35 @@ namespace NzbDrone.Core.MediaFiles.EpisodeImport.Manual
         public List<int> EpisodeIds { get; set; }
         public QualityModel Quality { get; set; }
         public string DownloadId { get; set; }
+
+        public bool Equals(ManualImportFile other)
+        {
+            if (other == null)
+            {
+                return false;
+            }
+
+            return Path.PathEquals(other.Path);
+        }
+
+        public override bool Equals(object obj)
+        {
+            if (obj == null)
+            {
+                return false;
+            }
+
+            if (obj.GetType() != GetType())
+            {
+                return false;
+            }
+
+            return Path.PathEquals(((ManualImportFile)obj).Path);
+        }
+
+        public override int GetHashCode()
+        {
+            return Path != null ? Path.GetHashCode() : 0;
+        }
     }
 }
diff --git a/src/NzbDrone.Core/Messaging/Commands/CommandEqualityComparer.cs b/src/NzbDrone.Core/Messaging/Commands/CommandEqualityComparer.cs
index eabbec15f..65f21b935 100644
--- a/src/NzbDrone.Core/Messaging/Commands/CommandEqualityComparer.cs
+++ b/src/NzbDrone.Core/Messaging/Commands/CommandEqualityComparer.cs
@@ -49,10 +49,13 @@ namespace NzbDrone.Core.Messaging.Commands
 
                 if (typeof(IEnumerable).IsAssignableFrom(xProperty.PropertyType))
                 {
-                    var xValueCollection = ((IEnumerable)xValue).Cast<object>().OrderBy(t => t);
-                    var yValueCollection = ((IEnumerable)yValue).Cast<object>().OrderBy(t => t);
+                    var xValueCollection = ((IEnumerable)xValue).Cast<object>();
+                    var yValueCollection = ((IEnumerable)yValue).Cast<object>();
 
-                    if (!xValueCollection.SequenceEqual(yValueCollection))
+                    var xNotY = xValueCollection.Except(yValueCollection);
+                    var yNotX = yValueCollection.Except(xValueCollection);
+
+                    if (xNotY.Any() || yNotX.Any())
                     {
                         return false;
                     }