diff --git a/src/main/java/reactor/ipc/netty/channel/ChannelOperationsHandler.java b/src/main/java/reactor/ipc/netty/channel/ChannelOperationsHandler.java
index ca7664af12..d044b40d8c 100755
--- a/src/main/java/reactor/ipc/netty/channel/ChannelOperationsHandler.java
+++ b/src/main/java/reactor/ipc/netty/channel/ChannelOperationsHandler.java
@@ -692,6 +692,17 @@ public void onNext(Object t) {
 
 		@SuppressWarnings("FutureReturnValueIgnored")
 		private void onNextInternal(Object t, ChannelPromise promise) {
+			if (!parent.ctx.channel()
+			               .isActive()) {
+				cancel();
+				if (log.isDebugEnabled()) {
+					log.debug(format(parent.ctx.channel(), "Dropping pending write, " +
+							"since connection has been closed: {}"), t);
+				}
+				ReferenceCountUtil.release(t);
+				return;
+			}
+
 			produced++;
 
 			// Returned value is deliberately ignored
diff --git a/src/main/java/reactor/ipc/netty/http/client/HttpClientOperations.java b/src/main/java/reactor/ipc/netty/http/client/HttpClientOperations.java
index c1289ca798..b4a382f06e 100644
--- a/src/main/java/reactor/ipc/netty/http/client/HttpClientOperations.java
+++ b/src/main/java/reactor/ipc/netty/http/client/HttpClientOperations.java
@@ -271,7 +271,12 @@ protected void onInboundClose() {
 			return;
 		}
 		if (responseState == null) {
-			parentContext().fireContextError(new IOException("Connection closed prematurely"));
+			if (markSentBody()) {
+				parentContext().fireContextError(new IOException("Connection has been closed, while sending request body"));
+			}
+			else {
+				parentContext().fireContextError(new IOException("Connection closed prematurely"));
+			}
 			return;
 		}
 		super.onInboundError(new IOException("Connection closed prematurely"));
diff --git a/src/test/java/reactor/ipc/netty/http/server/HttpSendFileTests.java b/src/test/java/reactor/ipc/netty/http/server/HttpSendFileTests.java
index 75512a1407..89a0d00976 100644
--- a/src/test/java/reactor/ipc/netty/http/server/HttpSendFileTests.java
+++ b/src/test/java/reactor/ipc/netty/http/server/HttpSendFileTests.java
@@ -21,6 +21,7 @@
 import java.nio.ByteBuffer;
 import java.nio.channels.AsynchronousFileChannel;
 import java.nio.channels.CompletionHandler;
+import java.nio.charset.Charset;
 import java.nio.charset.StandardCharsets;
 import java.nio.file.FileSystem;
 import java.nio.file.FileSystems;
@@ -31,6 +32,7 @@
 import java.nio.file.StandardOpenOption;
 import java.time.Duration;
 import java.util.concurrent.atomic.AtomicLong;
+import java.util.function.BiFunction;
 import java.util.function.BiPredicate;
 import java.util.function.Consumer;
 import java.util.function.Function;
@@ -38,8 +40,10 @@
 import io.netty.buffer.ByteBuf;
 import io.netty.buffer.ByteBufAllocator;
 import io.netty.handler.codec.http.HttpHeaderNames;
+import io.netty.handler.codec.http.HttpHeaders;
 import io.netty.handler.codec.http.HttpMethod;
 import org.junit.Test;
+import org.reactivestreams.Publisher;
 import reactor.core.publisher.Flux;
 import reactor.core.publisher.FluxSink;
 import reactor.ipc.netty.NettyContext;
@@ -268,15 +272,29 @@ private void assertSendFile(Function<HttpServerResponse, NettyOutbound> fn, bool
 
 	@Test
 	public void sendFileAsync4096() throws IOException, URISyntaxException {
-		doTestSendFileAsync(4096);
+		doTestSendFileAsync((req, resp) -> resp.sendByteArray(req.receive()
+				                               .aggregate()
+				                               .asByteArray()),
+				4096, null);
+	}
+
+	@Test
+	public void sendFileAsync4096Negative() throws IOException, URISyntaxException {
+		doTestSendFileAsync((req, resp) -> resp.status(500)
+				                               .header(HttpHeaderNames.CONNECTION, "close"),
+				4096, "error".getBytes(Charset.defaultCharset()));
 	}
 
 	@Test
 	public void sendFileAsync1024() throws IOException, URISyntaxException {
-		doTestSendFileAsync(1024);
+		doTestSendFileAsync((req, resp) -> resp.sendByteArray(req.receive()
+				                               .aggregate()
+				                               .asByteArray()),
+				1024, null);
 	}
 
-	private void doTestSendFileAsync(int chunk) throws IOException, URISyntaxException {
+	private void doTestSendFileAsync(BiFunction<? super HttpServerRequest, ? super
+			HttpServerResponse, ? extends Publisher<Void>> fn, int chunk, byte[] expectedContent) throws IOException, URISyntaxException {
 		Path largeFile = Paths.get(getClass().getResource("/largeFile.txt").toURI());
 		Path tempFile = Files.createTempFile(largeFile.getParent(),"temp", ".txt");
 		tempFile.toFile().deleteOnExit();
@@ -307,9 +325,7 @@ private void doTestSendFileAsync(int chunk) throws IOException, URISyntaxExcepti
 
 		NettyContext context =
 				HttpServer.create(opt -> customizeServerOptions(opt.host("localhost")))
-				          .newHandler((req, resp) -> resp.sendByteArray(req.receive()
-				                                                           .aggregate()
-				                                                           .asByteArray()))
+				          .newHandler(fn)
 				          .block();
 		assertThat(context).isNotNull();
 
@@ -319,9 +335,14 @@ private void doTestSendFileAsync(int chunk) throws IOException, URISyntaxExcepti
 				          .flatMap(res -> res.receive()
 				                             .aggregate()
 				                             .asByteArray())
+				          .onErrorReturn(t ->
+				              t instanceof IOException &&
+				                  "Connection has been closed, while sending request body".equals(t.getMessage())
+				              ,
+				              "error".getBytes(Charset.defaultCharset()))
 				          .block();
 
-		assertThat(response).isEqualTo(Files.readAllBytes(tempFile));
+		assertThat(response).isEqualTo(expectedContent == null ? Files.readAllBytes(tempFile) : expectedContent);
 		context.dispose();
 	}