diff --git a/ballerina-tests/http2-tests/tests/http2_configuration_request_limit_config_test.bal b/ballerina-tests/http2-tests/tests/http2_configuration_request_limit_config_test.bal
index 83924c0dd3..92fe98ebed 100644
--- a/ballerina-tests/http2-tests/tests/http2_configuration_request_limit_config_test.bal
+++ b/ballerina-tests/http2-tests/tests/http2_configuration_request_limit_config_test.bal
@@ -145,28 +145,33 @@ function testHttp2ValidHeaderLength() returns error? {
 }
 
 //Tests the behaviour when header size is greater than the configured threshold
-// TODO: Enable after fixing this issue : https://github.com/ballerina-platform/ballerina-standard-library/issues/3963
-@test:Config {
-    enable: false
-}
+@test:Config {}
 function testHttp2InvalidHeaderLength() returns error? {
     http:Client limitClient = check new ("http://localhost:" + http2RequestLimitsTestPort3.toString(),
         http2Settings = {http2PriorKnowledge: true});
-    http:Response response = check limitClient->get("/lowRequestHeaderLimit/invalidHeaderSize", {"X-Test": getLargeHeader()});
+    http:Response|http:Error response = limitClient->get("/lowRequestHeaderLimit/invalidHeaderSize", {"X-Test": getLargeHeader()});
     //431 Request Header Fields Too Large
-    test:assertEquals(response.statusCode, 431, msg = "Found unexpected output");
+    if response is http:Error {
+        test:assertTrue(response is http:ClientError);
+        test:assertEquals(response.message(), "Header size exceeded max allowed size (600)");
+    } else {
+        test:assertEquals(response.statusCode, 431, msg = "Found unexpected output");
+    }
 }
 
 // Tests the fallback behaviour when header size is greater than the configured http2 service
 // TODO: Enable after fixing this issue : https://github.com/ballerina-platform/ballerina-standard-library/issues/3963
-@test:Config {
-    enable: false
-}
+@test:Config {}
 function testHttp2Http2ServiceInvalidHeaderLength() returns error? {
     http:Client limitClient = check new ("http://localhost:" + requestLimitsTestPort5.toString(),
         http2Settings = {http2PriorKnowledge: true});
-    http:Response response = check limitClient->get("/http2service/invalidHeaderSize", {"X-Test": getLargeHeader()});
-    test:assertEquals(response.statusCode, 431, msg = "Found unexpected output");
+    http:Response|http:Error response = limitClient->get("/http2service/invalidHeaderSize", {"X-Test": getLargeHeader()});
+    if response is http:Error {
+        test:assertTrue(response is http:ClientError);
+        test:assertEquals(response.message(), "Header size exceeded max allowed size (850)");
+    } else {
+        test:assertEquals(response.statusCode, 431, msg = "Found unexpected output");
+    }
 }
 
 //Tests the behaviour when payload size is greater than the configured threshold
diff --git a/changelog.md b/changelog.md
index 4e430bf06d..27f41de3df 100644
--- a/changelog.md
+++ b/changelog.md
@@ -14,6 +14,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
 ### Fixed
 - [Remove unused import from Http2StateUtil](https://github.com/ballerina-platform/ballerina-library/issues/5966)
 - [Fix client getting hanged when server closes connection in the ALPN handshake](https://github.com/ballerina-platform/ballerina-library/issues/6003)
+- [Fix client getting hanged when multiple requests are sent which exceed `maxHeaderSize`](https://github.com/ballerina-platform/ballerina-library/issues/6000)
 
 ## [2.10.5] - 2023-12-06
 
diff --git a/native/src/main/java/io/ballerina/stdlib/http/transport/contractimpl/common/states/Http2StateUtil.java b/native/src/main/java/io/ballerina/stdlib/http/transport/contractimpl/common/states/Http2StateUtil.java
index e8ed1daf54..e72fd6ae8a 100644
--- a/native/src/main/java/io/ballerina/stdlib/http/transport/contractimpl/common/states/Http2StateUtil.java
+++ b/native/src/main/java/io/ballerina/stdlib/http/transport/contractimpl/common/states/Http2StateUtil.java
@@ -43,6 +43,7 @@
 import io.netty.channel.ChannelFuture;
 import io.netty.channel.ChannelFutureListener;
 import io.netty.channel.ChannelHandlerContext;
+import io.netty.channel.ChannelPromise;
 import io.netty.handler.codec.http.DefaultLastHttpContent;
 import io.netty.handler.codec.http.HttpContent;
 import io.netty.handler.codec.http.HttpHeaderNames;
@@ -320,9 +321,13 @@ public static void writeHttp2Headers(ChannelHandlerContext ctx, OutboundMsgHolde
                 return;
             }
         }
-
-        encoder.writeHeaders(ctx, streamId, http2Headers, dependencyId, weight, false, 0, endStream,
-                             ctx.newPromise());
+        ChannelPromise promise = ctx.newPromise();
+        encoder.writeHeaders(ctx, streamId, http2Headers, dependencyId, weight, false, 0, endStream, promise);
+        promise.addListener((ChannelFutureListener) channelFuture -> {
+            if (!channelFuture.isSuccess()) {
+                outboundMsgHolder.getResponseFuture().notifyHttpListener(channelFuture.cause());
+            }
+        });
         encoder.flowController().writePendingBytes();
         ctx.flush();