diff --git a/src/NuGet.Server.Core/Infrastructure/JsonNetPackagesSerializer.cs b/src/NuGet.Server.Core/Infrastructure/JsonNetPackagesSerializer.cs
index cf82826c..487b3ac8 100644
--- a/src/NuGet.Server.Core/Infrastructure/JsonNetPackagesSerializer.cs
+++ b/src/NuGet.Server.Core/Infrastructure/JsonNetPackagesSerializer.cs
@@ -1,6 +1,7 @@
 // Copyright (c) .NET Foundation. All rights reserved.
 // Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information. 
 
+using System;
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
@@ -18,7 +19,8 @@ public class JsonNetPackagesSerializer
         private readonly JsonSerializer _serializer = new JsonSerializer
         {
             Formatting = Formatting.None,
-            NullValueHandling = NullValueHandling.Ignore
+            NullValueHandling = NullValueHandling.Ignore,
+            Converters = { new AbsoluteUriConverter() },
         };
 
         public void Serialize(IEnumerable<ServerPackage> packages, Stream stream)
@@ -51,5 +53,54 @@ public IEnumerable<ServerPackage> Deserialize(Stream stream)
                 return packages.Packages;
             }
         }
+
+        /// <summary>
+        /// This is necessary because Newtonsoft.Json creates <see cref="Uri"/> instances with
+        /// <see cref="UriKind.RelativeOrAbsolute"/> which treats UNC paths as relative. NuGet.Core uses
+        /// <see cref="UriKind.Absolute"/> which treats UNC paths as absolute. For more details, see:
+        /// https://github.com/JamesNK/Newtonsoft.Json/issues/2128
+        /// </summary>
+        private class AbsoluteUriConverter : JsonConverter
+        {
+            public override bool CanConvert(Type objectType)
+            {
+                return objectType == typeof(Uri);
+            }
+
+            public override object ReadJson(JsonReader reader, Type objectType, object existingValue, JsonSerializer serializer)
+            {
+                if (reader.TokenType == JsonToken.Null)
+                {
+                    return null;
+                }
+                else if (reader.TokenType == JsonToken.String)
+                {
+                    return new Uri((string)reader.Value, UriKind.Absolute);
+                }
+
+                throw new JsonSerializationException("The JSON value must be a string.");
+            }
+
+            public override void WriteJson(JsonWriter writer, object value, JsonSerializer serializer)
+            {
+                if (value == null)
+                {
+                    writer.WriteNull();
+                    return;
+                }
+
+                if (!(value is Uri uriValue))
+                {
+                    throw new JsonSerializationException("The value must be a URI.");
+                }
+
+                if (!uriValue.IsAbsoluteUri)
+                {
+                    throw new JsonSerializationException("The URI value must be an absolute Uri. Relative URI instances are not allowed.");
+                }
+
+                writer.WriteValue(uriValue.OriginalString);
+            }
+        }
     }
 }
\ No newline at end of file
diff --git a/test/NuGet.Server.Core.Tests/JsonNetPackagesSerializerTests.cs b/test/NuGet.Server.Core.Tests/JsonNetPackagesSerializerTests.cs
index 0f0a9f1a..42c0cea8 100644
--- a/test/NuGet.Server.Core.Tests/JsonNetPackagesSerializerTests.cs
+++ b/test/NuGet.Server.Core.Tests/JsonNetPackagesSerializerTests.cs
@@ -14,6 +14,37 @@ namespace NuGet.Server.Core.Tests
 {
     public class JsonNetPackagesSerializerTests
     {
+        [Fact]
+        public void RoundTripsUncPaths()
+        {
+            var originalPackages = GenerateServerPackages(1);
+            var originalPackage = originalPackages.Single();
+            originalPackage.IconUrl = new Uri("//testunc/test/a", UriKind.Absolute);
+            originalPackage.LicenseUrl = new Uri("//testunc/test/b", UriKind.Absolute);
+            originalPackage.ProjectUrl = new Uri("//testunc/test/c", UriKind.Absolute);
+            originalPackage.ReportAbuseUrl = new Uri("//testunc/test/d", UriKind.Absolute);
+            var serializer = new JsonNetPackagesSerializer();
+
+            // Act
+            var deserializedPackages = new List<ServerPackage>();
+            using (var memoryStream = new MemoryStream())
+            {
+                serializer.Serialize(originalPackages, memoryStream);
+
+                memoryStream.Position = 0;
+
+                deserializedPackages.AddRange(serializer.Deserialize(memoryStream));
+            }
+
+            // Assert
+            AssertPackagesAreEqual(originalPackages, deserializedPackages);
+            var deserializedPackage = deserializedPackages.Single();
+            Assert.True(deserializedPackage.IconUrl.IsAbsoluteUri, "The icon URL should still be absolute.");
+            Assert.True(deserializedPackage.LicenseUrl.IsAbsoluteUri, "The license URL should still be absolute.");
+            Assert.True(deserializedPackage.ProjectUrl.IsAbsoluteUri, "The project URL should still be absolute.");
+            Assert.True(deserializedPackage.ReportAbuseUrl.IsAbsoluteUri, "The report abuse URL should still be absolute.");
+        }
+
         [Fact]
         public void TestSerializationRoundTrip()
         {
@@ -33,14 +64,25 @@ public void TestSerializationRoundTrip()
             }
 
             // Assert
+            AssertPackagesAreEqual(originalPackages, deserializedPackages);
+        }
+
+        private static void AssertPackagesAreEqual(List<ServerPackage> originalPackages, List<ServerPackage> deserializedPackages)
+        {
             Assert.Equal(originalPackages.Count, deserializedPackages.Count);
             for (var i = 0; i < originalPackages.Count; i++)
             {
-                Assert.True(PublicPropertiesEqual(originalPackages[i], deserializedPackages[i], "DependencySets", "FrameworkAssemblies", "PackageAssemblyReferences", "AssemblyReferences"));
+                AssertPublicPropertiesEqual(
+                    originalPackages[i],
+                    deserializedPackages[i],
+                    "DependencySets",
+                    "FrameworkAssemblies",
+                    "PackageAssemblyReferences",
+                    "AssemblyReferences");
             }
         }
 
-        private static bool PublicPropertiesEqual<T>(T a, T b, params string[] ignoreProperties) where T : class
+        private static void AssertPublicPropertiesEqual<T>(T a, T b, params string[] ignoreProperties) where T : class
         {
             if (a != null && b != null)
             {
@@ -55,15 +97,15 @@ private static bool PublicPropertiesEqual<T>(T a, T b, params string[] ignorePro
 
                         if (selfValue != toValue && (selfValue == null || !selfValue.Equals(toValue)) && !(selfValue is IEnumerable))
                         {
-                            return false;
+                            Assert.False(true, $"The property '{pi.Name}' is not equal.");
                         }
                     }
                 }
 
-                return true;
+                return;
             }
 
-            return a == b;
+            Assert.Equal(a, b);
         }
 
         private static List<ServerPackage> GenerateServerPackages(int count)