diff --git a/docker/Instances/1/state.json b/docker/Instances/1/state.json
index 81ade68..ade1da7 100644
--- a/docker/Instances/1/state.json
+++ b/docker/Instances/1/state.json
@@ -3,7 +3,7 @@
     "installationName": "VisualStudio/public.d15rel/15.0.26116.0",
     "installationVersion": "15.0.26116",
     "installationPath": "C:\\VS\\Community",
-    "installDate": "2017-01-17T03:00:00Z",
+    "installDate": "2017-01-17T03:45:00Z",
     "product": {
         "id": "Microsoft.VisualStudio.Product.Community",
         "version": "15.0.26116.0",
diff --git a/src/VSSetup.PowerShell/Instance.cs b/src/VSSetup.PowerShell/Instance.cs
index ac0f238..604ee84 100644
--- a/src/VSSetup.PowerShell/Instance.cs
+++ b/src/VSSetup.PowerShell/Instance.cs
@@ -67,7 +67,7 @@ internal Instance(ISetupInstance2 instance)
                 () =>
                 {
                     var versionString = instance.GetInstallationVersion();
-                    if (Utilities.TryParseVersion(versionString, out Version version))
+                    if (Utilities.TryParseVersion(versionString, out var version))
                     {
                         return version.Normalize();
                     }
@@ -94,19 +94,13 @@ internal Instance(ISetupInstance2 instance)
             Utilities.TrySet(
                 ref displayName,
                 nameof(DisplayName),
-                () =>
-                {
-                    return instance.GetDisplayName(lcid);
-                },
+                () => instance.GetDisplayName(lcid),
                 OnError);
 
             Utilities.TrySet(
                 ref description,
                 nameof(Description),
-                () =>
-                {
-                    return instance.GetDescription(lcid);
-                },
+                () => instance.GetDescription(lcid),
                 OnError);
 
             Utilities.TrySet(
diff --git a/src/VSSetup.PowerShell/InstanceComparer.cs b/src/VSSetup.PowerShell/InstanceComparer.cs
new file mode 100644
index 0000000..d18b81f
--- /dev/null
+++ b/src/VSSetup.PowerShell/InstanceComparer.cs
@@ -0,0 +1,65 @@
+// <copyright file="InstanceComparer.cs" company="Microsoft Corporation">
+// Copyright (C) Microsoft Corporation. All rights reserved.
+// Licensed under the MIT license. See LICENSE.txt in the project root for license information.
+// </copyright>
+
+namespace Microsoft.VisualStudio.Setup
+{
+    using System;
+    using System.Collections.Generic;
+
+    /// <summary>
+    /// Compares instances of <see cref="Instance"/>.
+    /// </summary>
+    internal class InstanceComparer : IComparer<Instance>
+    {
+        /// <summary>
+        /// Gets an instance of the <see cref="InstanceComparer"/> that compares only the
+        /// <see cref="Instance.InstallationVersion"/> and <see cref="Instance.InstallDate"/> properties.
+        /// </summary>
+        public static readonly IComparer<Instance> VersionAndDate = new InstanceComparer();
+
+        /// <inheritdoc/>
+        public int Compare(Instance x, Instance y)
+        {
+            if (ReferenceEquals(x, y))
+            {
+                return 0;
+            }
+            else if (x is null)
+            {
+                return -1;
+            }
+            else if (y is null)
+            {
+                return 1;
+            }
+
+            var result = Compare(x.InstallationVersion, y.InstallationVersion);
+            if (result != 0)
+            {
+                return result;
+            }
+
+            return DateTime.Compare(x.InstallDate, y.InstallDate);
+        }
+
+        private static int Compare(Version x, Version y)
+        {
+            if (ReferenceEquals(x, y))
+            {
+                return 0;
+            }
+            else if (x is null)
+            {
+                return -1;
+            }
+            else if (y is null)
+            {
+                return 1;
+            }
+
+            return x.CompareTo(y);
+        }
+    }
+}
diff --git a/src/VSSetup.PowerShell/PowerShell/SelectInstanceCommand.cs b/src/VSSetup.PowerShell/PowerShell/SelectInstanceCommand.cs
index 273c8ae..90f9d6e 100644
--- a/src/VSSetup.PowerShell/PowerShell/SelectInstanceCommand.cs
+++ b/src/VSSetup.PowerShell/PowerShell/SelectInstanceCommand.cs
@@ -139,6 +139,12 @@ bool Contains(IEnumerable<PackageReference> packages, Func<PackageReference, str
                             select instance;
             }
 
+            if (Latest)
+            {
+                // Sort by the InstallationVersion then InstallDate so we can easily find the latest.
+                instances = instances.OrderBy(instance => instance, InstanceComparer.VersionAndDate);
+            }
+
             foreach (var instance in instances)
             {
                 if (Latest)
diff --git a/src/VSSetup.PowerShell/VSSetup.PowerShell.csproj b/src/VSSetup.PowerShell/VSSetup.PowerShell.csproj
index be1cdcb..d88bc83 100644
--- a/src/VSSetup.PowerShell/VSSetup.PowerShell.csproj
+++ b/src/VSSetup.PowerShell/VSSetup.PowerShell.csproj
@@ -51,6 +51,7 @@
     <Compile Include="Extensions.cs" />
     <Compile Include="FailedPackageReference.cs" />
     <Compile Include="Instance.cs" />
+    <Compile Include="InstanceComparer.cs" />
     <Compile Include="Module.cs" />
     <Compile Include="NativeMethods.cs" />
     <Compile Include="PackageReference.cs" />
@@ -112,4 +113,4 @@
     </PropertyGroup>
     <Error Condition="!Exists('..\..\packages\Nerdbank.GitVersioning.1.5.97\build\portable-net+win+wpa+wp+sl+netmf+MonoAndroid+MonoTouch+Xamarin.iOS\Nerdbank.GitVersioning.targets')" Text="$([System.String]::Format('$(ErrorText)', '..\..\packages\Nerdbank.GitVersioning.1.5.97\build\portable-net+win+wpa+wp+sl+netmf+MonoAndroid+MonoTouch+Xamarin.iOS\Nerdbank.GitVersioning.targets'))" />
   </Target>
-</Project>
+</Project>
\ No newline at end of file
diff --git a/test/VSSetup.PowerShell.Test/InstanceComparerTests.cs b/test/VSSetup.PowerShell.Test/InstanceComparerTests.cs
new file mode 100644
index 0000000..9e08036
--- /dev/null
+++ b/test/VSSetup.PowerShell.Test/InstanceComparerTests.cs
@@ -0,0 +1,61 @@
+// <copyright file="InstanceComparerTests.cs" company="Microsoft Corporation">
+// Copyright (C) Microsoft Corporation. All rights reserved.
+// Licensed under the MIT license. See LICENSE.txt in the project root for license information.
+// </copyright>
+
+namespace Microsoft.VisualStudio.Setup
+{
+    using System;
+    using System.Collections.Generic;
+    using System.Runtime.InteropServices.ComTypes;
+    using Microsoft.VisualStudio.Setup.Configuration;
+    using Moq;
+    using Xunit;
+
+    public class InstanceComparerTests
+    {
+        public static IEnumerable<object[]> GetCompareVersionAndDateData()
+        {
+            var empty = new string[0];
+
+            var v1 = new Version(1, 0);
+            var v2 = new Version(2, 0);
+
+            var ft1 = new FILETIME { dwHighDateTime = 1 };
+            var ft2 = new FILETIME { dwHighDateTime = 2 };
+
+            Instance Mock(Version v = null, FILETIME ft = default(FILETIME))
+            {
+                var mock = new Mock<ISetupInstance2>();
+                mock.As<ISetupPropertyStore>().Setup(x => x.GetNames()).Returns(empty);
+
+                mock.Setup(x => x.GetInstallationVersion()).Returns(v?.ToString());
+                mock.Setup(x => x.GetInstallDate()).Returns(ft);
+
+                return new Instance(mock.Object);
+            }
+
+            return new[]
+            {
+                new object[] { null, null, 0 },
+                new object[] { null, Mock(), -1 },
+                new object[] { Mock(), null, 1 },
+                new object[] { Mock(), Mock(v1), -1 },
+                new object[] { Mock(v1), Mock(), 1 },
+                new object[] { Mock(v1), Mock(v1), 0 },
+                new object[] { Mock(v1), Mock(v2), -1 },
+                new object[] { Mock(v2), Mock(v1), 1 },
+                new object[] { Mock(v2, ft1), Mock(v2, ft2), -1 },
+                new object[] { Mock(v2, ft2), Mock(v2, ft1), 1 },
+            };
+        }
+
+        [Theory]
+        [MemberData(nameof(GetCompareVersionAndDateData))]
+        public void CompareVersionAndDate(Instance x, Instance y, int expected)
+        {
+            var actual = InstanceComparer.VersionAndDate.Compare(x, y);
+            Assert.Equal(expected, actual);
+        }
+    }
+}
diff --git a/test/VSSetup.PowerShell.Test/VSSetup.PowerShell.Test.csproj b/test/VSSetup.PowerShell.Test/VSSetup.PowerShell.Test.csproj
index 562af93..8cfb823 100644
--- a/test/VSSetup.PowerShell.Test/VSSetup.PowerShell.Test.csproj
+++ b/test/VSSetup.PowerShell.Test/VSSetup.PowerShell.Test.csproj
@@ -90,6 +90,7 @@
     <Compile Include="PowerShell\SelectInstanceCommandTests.cs" />
     <Compile Include="Properties\AssemblyInfo.cs" />
     <Compile Include="ReadOnlyDictionaryTests.cs" />
+    <Compile Include="InstanceComparerTests.cs" />
     <Compile Include="UtilitiesTests.cs" />
     <Compile Include="ValidateTests.cs" />
   </ItemGroup>