diff --git a/Emby.Dlna/Eventing/DlnaEventManager.cs b/Emby.Dlna/Eventing/DlnaEventManager.cs
index c0eacf5d83..ecbbdf9df9 100644
--- a/Emby.Dlna/Eventing/DlnaEventManager.cs
+++ b/Emby.Dlna/Eventing/DlnaEventManager.cs
@@ -164,7 +164,7 @@ namespace Emby.Dlna.Eventing
 
             try
             {
-                using var response = await _httpClientFactory.CreateClient(NamedClient.Default)
+                using var response = await _httpClientFactory.CreateClient(NamedClient.DirectIp)
                     .SendAsync(options, HttpCompletionOption.ResponseHeadersRead).ConfigureAwait(false);
             }
             catch (OperationCanceledException)
diff --git a/Jellyfin.Networking/HappyEyeballs/HttpClientExtension.cs b/Jellyfin.Networking/HappyEyeballs/HttpClientExtension.cs
new file mode 100644
index 0000000000..59e6956c71
--- /dev/null
+++ b/Jellyfin.Networking/HappyEyeballs/HttpClientExtension.cs
@@ -0,0 +1,120 @@
+/*
+The MIT License (MIT)
+
+Copyright (c) .NET Foundation and Contributors
+
+All rights reserved.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.
+*/
+
+using System.IO;
+using System.Net.Http;
+using System.Net.Sockets;
+using System.Threading;
+using System.Threading.Tasks;
+
+namespace Jellyfin.Networking.HappyEyeballs
+{
+    /// <summary>
+    /// Defines the <see cref="HttpClientExtension"/> class.
+    ///
+    /// Implementation taken from https://github.com/ppy/osu-framework/pull/4191 .
+    /// </summary>
+    public static class HttpClientExtension
+    {
+        /// <summary>
+        /// Gets or sets a value indicating whether the client should use IPv6.
+        /// </summary>
+        public static bool UseIPv6 { get; set; } = true;
+
+        /// <summary>
+        /// Implements the httpclient callback method.
+        /// </summary>
+        /// <param name="context">The <see cref="SocketsHttpConnectionContext"/> instance.</param>
+        /// <param name="cancellationToken">The <see cref="CancellationToken"/> instance.</param>
+        /// <returns>The http steam.</returns>
+        public static async ValueTask<Stream> OnConnect(SocketsHttpConnectionContext context, CancellationToken cancellationToken)
+        {
+            if (!UseIPv6)
+            {
+                return await AttemptConnection(AddressFamily.InterNetwork, context, cancellationToken).ConfigureAwait(false);
+            }
+
+            using var cancelIPv6 = CancellationTokenSource.CreateLinkedTokenSource(cancellationToken);
+            var tryConnectAsyncIPv6 = AttemptConnection(AddressFamily.InterNetworkV6, context, cancelIPv6.Token);
+
+            // GetAwaiter().GetResult() is used instead of .Result as this results in improved exception handling.
+            // The tasks have already been completed.
+            // See https://github.com/dotnet/corefx/pull/29792/files#r189415885 for more details.
+            if (await Task.WhenAny(tryConnectAsyncIPv6, Task.Delay(200, cancelIPv6.Token)).ConfigureAwait(false) == tryConnectAsyncIPv6 && tryConnectAsyncIPv6.IsCompletedSuccessfully)
+            {
+                cancelIPv6.Cancel();
+                return tryConnectAsyncIPv6.GetAwaiter().GetResult();
+            }
+
+            using var cancelIPv4 = CancellationTokenSource.CreateLinkedTokenSource(cancellationToken);
+            var tryConnectAsyncIPv4 = AttemptConnection(AddressFamily.InterNetwork, context, cancelIPv4.Token);
+
+            if (await Task.WhenAny(tryConnectAsyncIPv6, tryConnectAsyncIPv4).ConfigureAwait(false) == tryConnectAsyncIPv6)
+            {
+                if (tryConnectAsyncIPv6.IsCompletedSuccessfully)
+                {
+                    cancelIPv4.Cancel();
+                    return tryConnectAsyncIPv6.GetAwaiter().GetResult();
+                }
+
+                return tryConnectAsyncIPv4.GetAwaiter().GetResult();
+            }
+            else
+            {
+                if (tryConnectAsyncIPv4.IsCompletedSuccessfully)
+                {
+                    cancelIPv6.Cancel();
+                    return tryConnectAsyncIPv4.GetAwaiter().GetResult();
+                }
+
+                return tryConnectAsyncIPv6.GetAwaiter().GetResult();
+            }
+        }
+
+        private static async Task<Stream> AttemptConnection(AddressFamily addressFamily, SocketsHttpConnectionContext context, CancellationToken cancellationToken)
+        {
+            // The following socket constructor will create a dual-mode socket on systems where IPV6 is available.
+            var socket = new Socket(addressFamily, SocketType.Stream, ProtocolType.Tcp)
+            {
+                // Turn off Nagle's algorithm since it degrades performance in most HttpClient scenarios.
+                NoDelay = true
+            };
+
+            try
+            {
+                await socket.ConnectAsync(context.DnsEndPoint, cancellationToken).ConfigureAwait(false);
+                // The stream should take the ownership of the underlying socket,
+                // closing it when it's disposed.
+                return new NetworkStream(socket, ownsSocket: true);
+            }
+            catch
+            {
+                socket.Dispose();
+                throw;
+            }
+        }
+    }
+}
diff --git a/Jellyfin.Networking/Manager/NetworkManager.cs b/Jellyfin.Networking/Manager/NetworkManager.cs
index a6d5252ffc..afb0538205 100644
--- a/Jellyfin.Networking/Manager/NetworkManager.cs
+++ b/Jellyfin.Networking/Manager/NetworkManager.cs
@@ -592,6 +592,7 @@ namespace Jellyfin.Networking.Manager
 
             IsIP4Enabled = Socket.OSSupportsIPv4 && config.EnableIPV4;
             IsIP6Enabled = Socket.OSSupportsIPv6 && config.EnableIPV6;
+            HappyEyeballs.HttpClientExtension.UseIPv6 = IsIP6Enabled;
 
             if (!IsIP6Enabled && !IsIP4Enabled)
             {
@@ -836,9 +837,19 @@ namespace Jellyfin.Networking.Manager
             try
             {
                 await Task.Delay(2000).ConfigureAwait(false);
-                InitialiseInterfaces();
-                // Recalculate LAN caches.
-                InitialiseLAN(_configurationManager.GetNetworkConfiguration());
+
+                var config = _configurationManager.GetNetworkConfiguration();
+                // Have we lost IPv6 capability?
+                if (IsIP6Enabled && !Socket.OSSupportsIPv6)
+                {
+                    UpdateSettings(config);
+                }
+                else
+                {
+                    InitialiseInterfaces();
+                    // Recalculate LAN caches.
+                    InitialiseLAN(config);
+                }
 
                 NetworkChanged?.Invoke(this, EventArgs.Empty);
             }
diff --git a/Jellyfin.Server/Startup.cs b/Jellyfin.Server/Startup.cs
index 56f5c4796e..57efd5820b 100644
--- a/Jellyfin.Server/Startup.cs
+++ b/Jellyfin.Server/Startup.cs
@@ -8,6 +8,7 @@ using System.Text;
 using Jellyfin.Api.Middleware;
 using Jellyfin.MediaEncoding.Hls.Extensions;
 using Jellyfin.Networking.Configuration;
+using Jellyfin.Networking.HappyEyeballs;
 using Jellyfin.Server.Extensions;
 using Jellyfin.Server.HealthChecks;
 using Jellyfin.Server.Implementations;
@@ -26,6 +27,7 @@ using Microsoft.Extensions.Configuration;
 using Microsoft.Extensions.DependencyInjection;
 using Microsoft.Extensions.FileProviders;
 using Microsoft.Extensions.Hosting;
+using Microsoft.VisualBasic;
 using Prometheus;
 
 namespace Jellyfin.Server
@@ -78,6 +80,13 @@ namespace Jellyfin.Server
             var acceptJsonHeader = new MediaTypeWithQualityHeaderValue(MediaTypeNames.Application.Json, 1.0);
             var acceptXmlHeader = new MediaTypeWithQualityHeaderValue(MediaTypeNames.Application.Xml, 0.9);
             var acceptAnyHeader = new MediaTypeWithQualityHeaderValue("*/*", 0.8);
+            Func<IServiceProvider, HttpMessageHandler> eyeballsHttpClientHandlerDelegate = (_) => new SocketsHttpHandler()
+            {
+                AutomaticDecompression = DecompressionMethods.All,
+                RequestHeaderEncodingSelector = (_, _) => Encoding.UTF8,
+                ConnectCallback = HttpClientExtension.OnConnect
+            };
+
             Func<IServiceProvider, HttpMessageHandler> defaultHttpClientHandlerDelegate = (_) => new SocketsHttpHandler()
             {
                 AutomaticDecompression = DecompressionMethods.All,
@@ -91,7 +100,7 @@ namespace Jellyfin.Server
                     c.DefaultRequestHeaders.Accept.Add(acceptXmlHeader);
                     c.DefaultRequestHeaders.Accept.Add(acceptAnyHeader);
                 })
-                .ConfigurePrimaryHttpMessageHandler(defaultHttpClientHandlerDelegate);
+                .ConfigurePrimaryHttpMessageHandler(eyeballsHttpClientHandlerDelegate);
 
             services.AddHttpClient(NamedClient.MusicBrainz, c =>
                 {
@@ -100,6 +109,15 @@ namespace Jellyfin.Server
                     c.DefaultRequestHeaders.Accept.Add(acceptXmlHeader);
                     c.DefaultRequestHeaders.Accept.Add(acceptAnyHeader);
                 })
+                .ConfigurePrimaryHttpMessageHandler(eyeballsHttpClientHandlerDelegate);
+
+            services.AddHttpClient(NamedClient.DirectIp, c =>
+                {
+                    c.DefaultRequestHeaders.UserAgent.Add(productHeader);
+                    c.DefaultRequestHeaders.Accept.Add(acceptJsonHeader);
+                    c.DefaultRequestHeaders.Accept.Add(acceptXmlHeader);
+                    c.DefaultRequestHeaders.Accept.Add(acceptAnyHeader);
+                })
                 .ConfigurePrimaryHttpMessageHandler(defaultHttpClientHandlerDelegate);
 
             services.AddHttpClient(NamedClient.Dlna, c =>
diff --git a/MediaBrowser.Common/Net/NamedClient.cs b/MediaBrowser.Common/Net/NamedClient.cs
index a6cacd4f17..9c5544b0ff 100644
--- a/MediaBrowser.Common/Net/NamedClient.cs
+++ b/MediaBrowser.Common/Net/NamedClient.cs
@@ -1,4 +1,4 @@
-namespace MediaBrowser.Common.Net
+namespace MediaBrowser.Common.Net
 {
     /// <summary>
     /// Registered http client names.
@@ -6,7 +6,7 @@
     public static class NamedClient
     {
         /// <summary>
-        /// Gets the value for the default named http client.
+        /// Gets the value for the default named http client which implements happy eyeballs.
         /// </summary>
         public const string Default = nameof(Default);
 
@@ -19,5 +19,10 @@
         /// Gets the value for the DLNA named http client.
         /// </summary>
         public const string Dlna = nameof(Dlna);
+
+        /// <summary>
+        /// Non happy eyeballs implementation.
+        /// </summary>
+        public const string DirectIp = nameof(DirectIp);
     }
 }