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 147f38bac6..a0f7192049 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
@@ -142,23 +142,31 @@ private[netty] object NettyConnectionPool {
   }
 
   /**
-   * Refreshes the idle timeout handler on the channel pipeline.
+   * Attempts to refresh the idle timeout handler on the channel pipeline.
    * @return
    *   true if the handler was successfully refreshed prior to the channel being
-   *   closed
+   *   closed and the channel is still open.
+   *
+   *   true if the `timeout` is None and the channel is still open.
+   *
+   *   false of the channel is closed.
    */
   private def refreshIdleTimeoutHandler(
     channel: JChannel,
-    timeout: Duration,
-  ): Boolean = {
-    channel
-      .pipeline()
-      .replace(
-        Names.ReadTimeoutHandler,
-        Names.ReadTimeoutHandler,
-        new ReadTimeoutHandler(timeout.toMillis, TimeUnit.MILLISECONDS),
-      )
-    channel.isOpen
+    timeout: Option[Duration],
+  )(implicit trace: Trace): Task[Boolean] = {
+    ZIO.attempt {
+      timeout.map { timeout =>
+        channel
+          .pipeline()
+          .replace(
+            Names.ReadTimeoutHandler,
+            Names.ReadTimeoutHandler,
+            new ReadTimeoutHandler(timeout.toMillis, TimeUnit.MILLISECONDS),
+          )
+      }
+    }.when(channel.isOpen)
+      .as(channel.isOpen)
   }
 
   private final class ReadTimeoutErrorHandler(nettyRuntime: NettyRuntime)(implicit trace: Trace)
@@ -256,10 +264,12 @@ private[netty] object NettyConnectionPool {
         // We retry a few times hoping to obtain an open channel
         // NOTE: We need to release the channel before retrying, so that it can be closed and removed from the pool
         // We do that in a forked fiber so that we don't "block" the current fiber while the new resource is obtained
-        if (channel.isOpen && idleTimeout.fold(true)(refreshIdleTimeoutHandler(channel, _)))
-          ZIO.succeed(channel)
-        else
-          invalidate(channel) *> release.forkDaemon *> ZIO.fail(None)
+
+        refreshIdleTimeoutHandler(channel, idleTimeout).flatMap {
+          case true  => ZIO.succeed(channel)
+          case false => invalidate(channel) *> release.forkDaemon *> ZIO.fail(None)
+        }
+
       }
         .retry(retrySchedule(key))
         .catchAll {