diff --git a/zio-http/jvm/src/main/scala/zio/http/netty/client/NettyConnectionPool.scala b/zio-http/jvm/src/main/scala/zio/http/netty/client/NettyConnectionPool.scala
index ee5b672560..d2fdf42def 100644
--- a/zio-http/jvm/src/main/scala/zio/http/netty/client/NettyConnectionPool.scala
+++ b/zio-http/jvm/src/main/scala/zio/http/netty/client/NettyConnectionPool.scala
@@ -16,7 +16,7 @@
 
 package zio.http.netty.client
 
-import java.net.InetSocketAddress
+import java.net.{Inet6Address, InetAddress, InetSocketAddress}
 import java.util.concurrent.TimeUnit
 
 import zio._
@@ -36,6 +36,8 @@ private[netty] trait NettyConnectionPool extends ConnectionPool[JChannel]
 
 private[netty] object NettyConnectionPool {
 
+  private val HappyEyeballsDelay: Duration = 250.millis
+
   protected def createChannel(
     channelFactory: JChannelFactory[JChannel],
     eventLoopGroup: JEventLoopGroup,
@@ -106,38 +108,150 @@ private[netty] object NettyConnectionPool {
 
     for {
       resolvedHosts <- dnsResolver.resolve(location.host)
-      hosts         <- Random.shuffle(resolvedHosts.toList)
-      hostsNec      <- ZIO.succeed(NonEmptyChunk.fromIterable(hosts.head, hosts.tail))
-      ch            <- collectFirstSuccess(hostsNec) { host =>
-        ZIO.suspend {
-          val bootstrap = new Bootstrap()
-            .channelFactory(channelFactory)
-            .group(eventLoopGroup)
-            .remoteAddress(new InetSocketAddress(host, location.port))
-            .withOption[Integer](ChannelOption.CONNECT_TIMEOUT_MILLIS, connectionTimeout.map(_.toMillis.toInt))
-            .handler(initializer)
-          localAddress.foreach(bootstrap.localAddress)
-
-          val channelFuture = bootstrap.connect()
-          val ch            = channelFuture.channel()
-          Scope.addFinalizer {
-            NettyFutureExecutor.executed {
-              channelFuture.cancel(true)
-              ch.close()
-            }.when(ch.isOpen).ignoreLogged
-          } *> NettyFutureExecutor.executed(channelFuture).as(ch)
-        }
-      }
+      ch            <-
+        // Use Happy Eyeballs algorithm
+        happyEyeballsConnect(
+          resolvedHosts,
+          channelFactory,
+          eventLoopGroup,
+          location,
+          initializer,
+          connectionTimeout,
+          localAddress,
+        )
     } yield ch
   }
 
-  private def collectFirstSuccess[R, E, A, B](
-    as: NonEmptyChunk[A],
-  )(f: A => ZIO[R, E, B])(implicit trace: Trace): ZIO[R, E, B] = {
-    ZIO.suspendSucceed {
-      val it                 = as.iterator
-      def loop: ZIO[R, E, B] = f(it.next()).catchAll(e => if (it.hasNext) loop else ZIO.fail(e))
-      loop
+  /**
+   * Attempts to connect to a single address.
+   */
+  private def connectToAddress(
+    host: InetAddress,
+    channelFactory: JChannelFactory[JChannel],
+    eventLoopGroup: JEventLoopGroup,
+    location: URL.Location.Absolute,
+    initializer: ChannelInitializer[JChannel],
+    connectionTimeout: Option[Duration],
+    localAddress: Option[InetSocketAddress],
+  )(implicit trace: Trace): ZIO[Scope, Throwable, JChannel] = {
+    ZIO.suspend {
+      val bootstrap = new Bootstrap()
+        .channelFactory(channelFactory)
+        .group(eventLoopGroup)
+        .remoteAddress(new InetSocketAddress(host, location.port))
+        .withOption[Integer](ChannelOption.CONNECT_TIMEOUT_MILLIS, connectionTimeout.map(_.toMillis.toInt))
+        .handler(initializer)
+      localAddress.foreach(bootstrap.localAddress)
+
+      val channelFuture = bootstrap.connect()
+      val ch            = channelFuture.channel()
+      Scope.addFinalizer {
+        NettyFutureExecutor.executed {
+          channelFuture.cancel(true)
+          ch.close()
+        }.whenDiscard(ch.isOpen).ignoreLogged
+      }.uninterruptible *> NettyFutureExecutor.executed(channelFuture).as(ch)
+    }
+  }
+
+  /**
+   * Returns a sequence of connection attempts with their delays. Per RFC 8305,
+   * we start with IPv6, then after firstAddressFamilyDelay we try IPv4, then
+   * alternate between families.
+   */
+  private def sortAddresses(resolvedHosts: Chunk[InetAddress]): List[InetAddress] = {
+    val (ipv6Addresses, ipv4Addresses) = resolvedHosts.partition(_.isInstanceOf[Inet6Address])
+    val ipv6Iter                       = ipv6Addresses.iterator
+    val ipv4Iter                       = ipv4Addresses.iterator
+    val builder                        = List.newBuilder[InetAddress]
+    builder.sizeHint(resolvedHosts.size)
+
+    // Alternate between families
+    var useIpv6 = true
+    while (ipv6Iter.hasNext || ipv4Iter.hasNext) {
+
+      if (useIpv6 && ipv6Iter.hasNext) {
+        builder += ipv6Iter.next()
+      } else if (ipv4Iter.hasNext) {
+        builder += ipv4Iter.next()
+      } else if (ipv6Iter.hasNext) {
+        builder += ipv6Iter.next()
+      }
+
+      useIpv6 = !useIpv6
+    }
+
+    builder.result()
+  }
+
+  /**
+   * Implements Happy Eyeballs (RFC 8305) connection algorithm. Races connection
+   * attempts to IPv6 and IPv4 addresses with staggered delays.
+   */
+  private def happyEyeballsConnect(
+    resolvedHosts: Chunk[InetAddress],
+    channelFactory: JChannelFactory[JChannel],
+    eventLoopGroup: JEventLoopGroup,
+    location: URL.Location.Absolute,
+    initializer: ChannelInitializer[JChannel],
+    connectionTimeout: Option[Duration],
+    localAddress: Option[InetSocketAddress],
+  )(implicit trace: Trace): ZIO[Scope, Throwable, JChannel] = {
+
+    if (resolvedHosts.isEmpty) {
+      ZIO.fail(new RuntimeException("No addresses to connect to"))
+    } else if (resolvedHosts.size == 1) {
+      connectToAddress(
+        resolvedHosts.head,
+        channelFactory,
+        eventLoopGroup,
+        location,
+        initializer,
+        connectionTimeout,
+        localAddress,
+      )
+    } else {
+      val addresses = sortAddresses(resolvedHosts)
+      for {
+        lastFailed <- Queue.bounded[Unit](requestedCapacity = 1)
+        successful <- Ref.make(List.empty[JChannel])
+        _          <- ZIO.raceAll(
+          connectToAddress(
+            addresses.head,
+            channelFactory,
+            eventLoopGroup,
+            location,
+            initializer,
+            connectionTimeout,
+            localAddress,
+          ).onExit {
+            case e: Exit.Success[JChannel] => successful.update(channels => channels :+ e.value)
+            case _: Exit.Failure[_]        => lastFailed.offer(())
+          },
+          addresses.tail.zipWithIndex.map { case (address, index) =>
+            ZIO.sleep(HappyEyeballsDelay * index.toDouble).raceFirst(lastFailed.take).ignore *>
+              connectToAddress(
+                address,
+                channelFactory,
+                eventLoopGroup,
+                location,
+                initializer,
+                connectionTimeout,
+                localAddress,
+              ).onExit {
+                case e: Exit.Success[JChannel] => successful.update(channels => channels :+ e.value)
+                case _: Exit.Failure[_]        => lastFailed.offer(())
+              }
+          },
+        )
+        channels   <- successful.get
+        channel    <- channels.headOption match {
+          case ch: Some[JChannel] => ZIO.succeed(ch.value)
+          case None               => ZIO.fail(new RuntimeException("All connection attempts failed"))
+        }
+        _          <- ZIO.foreachDiscard(channels.tail)(ch => ZIO.attempt(ch.close()))
+      } yield channel
+
     }
   }