diff --git a/Dalamud/Networking/Http/HappyEyeballsCallback.cs b/Dalamud/Networking/Http/HappyEyeballsCallback.cs
index 222fef622..af854fb2c 100644
--- a/Dalamud/Networking/Http/HappyEyeballsCallback.cs
+++ b/Dalamud/Networking/Http/HappyEyeballsCallback.cs
@@ -1,12 +1,14 @@
 using System;
-using System.Collections.Concurrent;
 using System.Collections.Generic;
 using System.IO;
+using System.Linq;
 using System.Net;
 using System.Net.Http;
 using System.Net.Sockets;
 using System.Threading;
 using System.Threading.Tasks;
+
+using Dalamud.Logging.Internal;
 using Dalamud.Utility;
 
 namespace Dalamud.Networking.Http;
@@ -14,34 +16,36 @@ namespace Dalamud.Networking.Http;
 // Inspired by and adapted from https://github.com/jellyfin/jellyfin/pull/8598
 
 /// <summary>
-/// A class to provide a <see cref="SocketsHttpHandler.ConnectCallback"/> method (and tracked state) to implement a
-/// variant of the Happy Eyeballs algorithm for HTTP connections to dual-stack servers.
-///
-/// Each instance of this class tracks its own state.
+/// A class to provide a <see cref="SocketsHttpHandler.ConnectCallback"/> method to implement a variant of the Happy
+/// Eyeballs algorithm for HTTP connections to dual-stack servers.
 /// </summary>
 public class HappyEyeballsCallback : IDisposable
 {
-    private readonly ConcurrentDictionary<DnsEndPoint, AddressFamily> addressFamilyCache = new();
+    private static readonly ModuleLog Log = new("HTTP");
 
-    private readonly AddressFamily? forcedAddressFamily;
-    private readonly int ipv6GracePeriod;
+    /*
+     * ToDo: Eventually add in some kind of state management to cache DNS and IP Family.
+     * For now, this is ignored as the HTTPClient will keep connections alive, but there are benefits to sharing
+     * cached lookups between different clients. We just need to be able to easily expire those lookups first.
+     */
+
+    private readonly AddressFamily forcedAddressFamily;
+    private readonly int connectionBackoff;
 
     /// <summary>
     /// Initializes a new instance of the <see cref="HappyEyeballsCallback"/> class.
     /// </summary>
     /// <param name="forcedAddressFamily">Optional override to force a specific AddressFamily.</param>
-    /// <param name="ipv6GracePeriod">Grace period for IPv6 connectivity before starting IPv4 attempt.</param>
-    public HappyEyeballsCallback(AddressFamily? forcedAddressFamily = null, int ipv6GracePeriod = 100)
+    /// <param name="connectionBackoff">Backoff time between concurrent connection attempts.</param>
+    public HappyEyeballsCallback(AddressFamily? forcedAddressFamily = null, int connectionBackoff = 75)
     {
-        this.forcedAddressFamily = forcedAddressFamily;
-        this.ipv6GracePeriod = ipv6GracePeriod;
+        this.forcedAddressFamily = forcedAddressFamily ?? AddressFamily.Unspecified;
+        this.connectionBackoff = connectionBackoff;
     }
 
     /// <inheritdoc/>
     public void Dispose()
     {
-        this.addressFamilyCache.Clear();
-
         GC.SuppressFinalize(this);
     }
 
@@ -53,75 +57,54 @@ public class HappyEyeballsCallback : IDisposable
     /// <returns>Returns a Stream for consumption by HttpClient.</returns>
     public async ValueTask<Stream> ConnectCallback(SocketsHttpConnectionContext context, CancellationToken token)
     {
-        var addressFamilyOverride = this.GetAddressFamilyOverride(context);
+        var sortedRecords = await this.GetSortedAddresses(context.DnsEndPoint.Host, token);
 
-        if (addressFamilyOverride.HasValue)
+        var linkedToken = CancellationTokenSource.CreateLinkedTokenSource(token);
+        var tasks = new List<Task<NetworkStream>>();
+
+        var delayCts = CancellationTokenSource.CreateLinkedTokenSource(linkedToken.Token);
+        for (var i = 0; i < sortedRecords.Count; i++)
         {
-            return this.AttemptConnection(addressFamilyOverride.Value, context, token).GetAwaiter().GetResult();
+            var record = sortedRecords[i];
+
+            delayCts.CancelAfter(this.connectionBackoff * i);
+
+            var task = this.AttemptConnection(record, context.DnsEndPoint.Port, linkedToken.Token, delayCts.Token);
+            tasks.Add(task);
+
+            var nextDelayCts = CancellationTokenSource.CreateLinkedTokenSource(linkedToken.Token);
+            _ = task.ContinueWith(_ => { nextDelayCts.Cancel(); }, TaskContinuationOptions.OnlyOnFaulted);
+            delayCts = nextDelayCts;
         }
 
-        using var linkedToken = CancellationTokenSource.CreateLinkedTokenSource(token);
+        var stream = await AsyncUtils.FirstSuccessfulTask(tasks).ConfigureAwait(false);
+        Log.Verbose($"Established connection to {context.DnsEndPoint.Host} at {stream.Socket.RemoteEndPoint}");
 
-        NetworkStream stream;
+        // If we're here, it means we have a successful connection. A failure to connect would have caused the above
+        // line to explode, so we're safe to clean everything up.
+        linkedToken.Cancel();
+        tasks.ForEach(task => { task.ContinueWith(this.CleanupConnectionTask); });
 
-        // Give IPv6 a chance to connect first.
-        // However, only give it ipv4WaitMillis to connect before throwing IPv4 into the mix.
-        var tryConnectIPv6 = this.AttemptConnection(AddressFamily.InterNetworkV6, context, linkedToken.Token);
-        var timedV6Attempt = Task.WhenAny(tryConnectIPv6, Task.Delay(this.ipv6GracePeriod, linkedToken.Token));
-
-        if (await timedV6Attempt == tryConnectIPv6 && tryConnectIPv6.IsCompletedSuccessfully)
-        {
-            stream = tryConnectIPv6.GetAwaiter().GetResult();
-        }
-        else
-        {
-            var race = AsyncUtils.FirstSuccessfulTask(new List<Task<NetworkStream>>
-            {
-                tryConnectIPv6,
-                this.AttemptConnection(AddressFamily.InterNetwork, context, linkedToken.Token),
-            });
-
-            // If our connections all fail, this will explode with an exception.
-            stream = race.GetAwaiter().GetResult();
-        }
-
-        this.addressFamilyCache[context.DnsEndPoint] = stream.Socket.AddressFamily;
         return stream;
     }
 
-    private AddressFamily? GetAddressFamilyOverride(SocketsHttpConnectionContext context)
+    private async Task<NetworkStream> AttemptConnection(IPAddress address, int port, CancellationToken token, CancellationToken delayToken)
     {
-        if (this.forcedAddressFamily.HasValue)
+        await AsyncUtils.CancellableDelay(-1, delayToken).ConfigureAwait(false);
+
+        if (token.IsCancellationRequested)
         {
-            return this.forcedAddressFamily.Value;
+            return Task.FromCanceled<NetworkStream>(token).Result;
         }
 
-        // Force IPv4 if IPv6 support isn't detected to avoid the resolution delay.
-        if (!Socket.OSSupportsIPv6)
-        {
-            return AddressFamily.InterNetwork;
-        }
-
-        if (this.addressFamilyCache.TryGetValue(context.DnsEndPoint, out var cachedValue))
-        {
-            // TODO: Find some way to delete this after a while.
-            return cachedValue;
-        }
-
-        return null;
-    }
-
-    private async Task<NetworkStream> AttemptConnection(
-        AddressFamily family, SocketsHttpConnectionContext context, CancellationToken token)
-    {
-        var socket = new Socket(family, SocketType.Stream, ProtocolType.Tcp)
+        var socket = new Socket(address.AddressFamily, SocketType.Stream, ProtocolType.Tcp)
         {
             NoDelay = true,
         };
 
         try
         {
-            await socket.ConnectAsync(context.DnsEndPoint, token).ConfigureAwait(false);
+            await socket.ConnectAsync(address, port, token).ConfigureAwait(false);
             return new NetworkStream(socket, ownsSocket: true);
         }
         catch
@@ -130,4 +113,31 @@ public class HappyEyeballsCallback : IDisposable
             throw;
         }
     }
+
+    private async Task<List<IPAddress>> GetSortedAddresses(string hostname, CancellationToken token)
+    {
+        // This method abuses DNS ordering and LINQ a bit. We can normally assume that "addresses" will be provided in
+        // the order the system wants to use. GroupBy will return its groups *in the order they're discovered*. Meaning,
+        // the first group created will always be the "preferred" group, and all other groups are in preference order.
+        // This means a straight zipper merge is nice and clean and gives us most -> least preferred, repeating.
+        var dnsRecords = await Dns.GetHostAddressesAsync(hostname, this.forcedAddressFamily, token);
+
+        var groups = dnsRecords
+                     .GroupBy(a => a.AddressFamily)
+                     .Select(g => g.Select(v => v)).ToArray();
+
+        return Util.ZipperMerge(groups).ToList();
+    }
+
+    private void CleanupConnectionTask(Task task)
+    {
+        // marks the exception as handled as well, nifty!
+        // will also handle canceled cases, which aren't explicitly faulted.
+        var exception = task.Exception;
+
+        if (task.IsFaulted)
+        {
+            Log.Verbose(exception!, "A HappyEyeballs connection task failed. Are there network issues?");
+        }
+    }
 }
diff --git a/Dalamud/Networking/Http/HappyHttpClient.cs b/Dalamud/Networking/Http/HappyHttpClient.cs
index 7183255c1..8459f1453 100644
--- a/Dalamud/Networking/Http/HappyHttpClient.cs
+++ b/Dalamud/Networking/Http/HappyHttpClient.cs
@@ -24,7 +24,7 @@ internal class HappyHttpClient : IDisposable, IServiceType
         this.SharedHttpClient = new HttpClient(new SocketsHttpHandler
         {
             AutomaticDecompression = DecompressionMethods.All,
-            ConnectCallback = new HappyEyeballsCallback().ConnectCallback,
+            ConnectCallback = this.SharedHappyEyeballsCallback.ConnectCallback,
         });
     }
 
@@ -40,8 +40,8 @@ internal class HappyHttpClient : IDisposable, IServiceType
     /// Gets a <see cref="HappyEyeballsCallback"/> meant to be shared across any custom <see cref="HttpClient"/>s that
     /// need to be made in other parts of the application.
     ///
-    /// This should be used when shared callback/IPv6 cache state is desired across multiple clients, as sharing the
-    /// SocketsHandler may lead to GC issues.
+    /// This should be used when shared callback state is desired across multiple clients, as sharing the SocketsHandler
+    /// may lead to GC issues.
     /// </summary>
     public HappyEyeballsCallback SharedHappyEyeballsCallback { get; }
 
diff --git a/Dalamud/Utility/AsyncUtils.cs b/Dalamud/Utility/AsyncUtils.cs
index c0e0d1cf0..d252bd5d5 100644
--- a/Dalamud/Utility/AsyncUtils.cs
+++ b/Dalamud/Utility/AsyncUtils.cs
@@ -13,7 +13,7 @@ public static class AsyncUtils
 {
     /// <summary>
     /// Race a set of tasks, returning either the first to succeed or an aggregate of all exceptions. This helper does
-    /// not perform any automatic cancellation of losing tasks.
+    /// not perform any automatic cancellation of losing tasks, nor does it handle exceptions of losing tasks.
     /// </summary>
     /// <remarks>Derived from <a href="https://stackoverflow.com/a/37529395">this StackOverflow post</a>.</remarks>
     /// <param name="tasks">A list of tasks to race.</param>
@@ -29,7 +29,7 @@ public static class AsyncUtils
         {
             task.ContinueWith(t =>
             {
-                if (task.IsCompletedSuccessfully)
+                if (t.IsCompletedSuccessfully)
                 {
                     tcs.TrySetResult(t.Result);
                 }
@@ -42,4 +42,19 @@ public static class AsyncUtils
 
         return tcs.Task;
     }
+
+    /// <summary>
+    /// Provide a <see cref="Task.Delay(int, CancellationToken)"/> that won't throw an exception when it's canceled.
+    /// </summary>
+    /// <inheritdoc cref="Task.Delay(int, CancellationToken)"/>
+    public static async Task CancellableDelay(int millisecondsDelay, CancellationToken cancellationToken)
+    {
+        try
+        {
+            await Task.Delay(millisecondsDelay, cancellationToken);
+        }
+        catch (TaskCanceledException)
+        {
+        }
+    }
 }
diff --git a/Dalamud/Utility/Util.cs b/Dalamud/Utility/Util.cs
index a6d2ad01c..ecf672caf 100644
--- a/Dalamud/Utility/Util.cs
+++ b/Dalamud/Utility/Util.cs
@@ -556,6 +556,56 @@ public static class Util
         Process.Start(process);
     }
 
+    /// <summary>
+    /// Perform a "zipper merge" (A, 1, B, 2, C, 3) of multiple enumerables, allowing for lists to end early.
+    /// </summary>
+    /// <param name="sources">A set of enumerable sources to combine.</param>
+    /// <typeparam name="TSource">The resulting type of the merged list to return.</typeparam>
+    /// <returns>A new enumerable, consisting of the final merge of all lists.</returns>
+    public static IEnumerable<TSource> ZipperMerge<TSource>(params IEnumerable<TSource>[] sources)
+    {
+        // Borrowed from https://codereview.stackexchange.com/a/263451, thank you!
+        var enumerators = new IEnumerator<TSource>[sources.Length];
+        try
+        {
+            for (var i = 0; i < sources.Length; i++)
+            {
+                enumerators[i] = sources[i].GetEnumerator();
+            }
+
+            var hasNext = new bool[enumerators.Length];
+
+            bool MoveNext()
+            {
+                var anyHasNext = false;
+                for (var i = 0; i < enumerators.Length; i++)
+                {
+                    anyHasNext |= hasNext[i] = enumerators[i].MoveNext();
+                }
+
+                return anyHasNext;
+            }
+
+            while (MoveNext())
+            {
+                for (var i = 0; i < enumerators.Length; i++)
+                {
+                    if (hasNext[i])
+                    {
+                        yield return enumerators[i].Current;
+                    }
+                }
+            }
+        }
+        finally
+        {
+            foreach (var enumerator in enumerators)
+            {
+                enumerator?.Dispose();
+            }
+        }
+    }
+
     /// <summary>
     /// Dispose this object.
     /// </summary>