diff --git a/src/main/java/io/vertx/core/http/impl/Http1xClientConnection.java b/src/main/java/io/vertx/core/http/impl/Http1xClientConnection.java
index c63a7fec396..3f7a3141cad 100644
--- a/src/main/java/io/vertx/core/http/impl/Http1xClientConnection.java
+++ b/src/main/java/io/vertx/core/http/impl/Http1xClientConnection.java
@@ -719,6 +719,7 @@ void handleException(Throwable cause) {
     void handleClosed(Throwable err) {
       if (err != null) {
         handleException(err);
+        promise.tryFail(err);
       }
       if (!closed) {
         closed = true;
diff --git a/src/test/java/io/vertx/core/http/Http1xTest.java b/src/test/java/io/vertx/core/http/Http1xTest.java
index f79f25fb985..94eefd7e37f 100644
--- a/src/test/java/io/vertx/core/http/Http1xTest.java
+++ b/src/test/java/io/vertx/core/http/Http1xTest.java
@@ -5438,4 +5438,39 @@ public void testRecycleConnectionOnRequestEnd() throws Exception {
     }
     await();
   }
+
+  @Test
+  public void testFailPendingRequestAllocationWhenConnectionIsClosed() throws Exception {
+    waitFor(2);
+    server.requestHandler(request -> {
+      HttpServerResponse resp = request.response();
+      resp.end().onComplete(onSuccess(v -> {
+        request.connection().close();
+      }));
+    });
+    startServer(testAddress);
+    client.close();
+    client = vertx.createHttpClient(new HttpClientOptions().setPipelining(true), new PoolOptions().setHttp1MaxSize(1));
+    for (int i = 0;i < 2;i++) {
+      int val = i;
+      Future<HttpClientRequest> fut = client.request(requestOptions);
+      fut.onComplete(ar -> {
+        switch (val) {
+          case 0:
+            assertTrue(ar.succeeded());
+            HttpClientRequest req = ar.result();
+            req.sendHead();
+            req.response().onComplete(onSuccess(resp -> {
+              complete();
+            }));
+            break;
+          case 1:
+            assertTrue(ar.failed());
+            complete();
+            break;
+        }
+      });
+    }
+    await();
+  }
 }