diff --git a/vertx-core/src/main/java/io/vertx/core/net/impl/tcp/NetSocketImpl.java b/vertx-core/src/main/java/io/vertx/core/net/impl/tcp/NetSocketImpl.java
index a78cbd8137b..daeddeaadcf 100644
--- a/vertx-core/src/main/java/io/vertx/core/net/impl/tcp/NetSocketImpl.java
+++ b/vertx-core/src/main/java/io/vertx/core/net/impl/tcp/NetSocketImpl.java
@@ -17,6 +17,7 @@
 import io.netty.channel.ChannelHandlerContext;
 import io.netty.channel.ChannelPromise;
 import io.netty.handler.ssl.SslHandler;
+import io.netty.handler.stream.ChunkedWriteHandler;
 import io.vertx.core.Future;
 import io.vertx.core.Handler;
 import io.vertx.core.buffer.Buffer;
@@ -169,6 +170,11 @@ private Future<Void> sslUpgrade(String serverName, SSLOptions sslOptions, ByteBu
               chctx.pipeline().addFirst("handshaker", handshaker);
               chctx.pipeline().addFirst("ssl", sslHandler);
             }
+            if (chctx.pipeline().get("chunkedWriter") == null) {
+              // The connection can no longer use zero-copy, sendFile needs a ChunkedWriteHandler to consume the
+              // chunked file it writes - the pipeline was set up without one since the channel was not encrypted
+              chctx.pipeline().addBefore(chctx.name(), "chunkedWriter", new ChunkedWriteHandler());
+            }
             channelPromise.addListener(p);
             doPause();
           } else {
diff --git a/vertx-core/src/test/java/io/vertx/tests/net/NetTest.java b/vertx-core/src/test/java/io/vertx/tests/net/NetTest.java
index c00503bef0e..9fba88b19b3 100755
--- a/vertx-core/src/test/java/io/vertx/tests/net/NetTest.java
+++ b/vertx-core/src/test/java/io/vertx/tests/net/NetTest.java
@@ -2480,6 +2480,70 @@ public void sendFileServerToClient(Checkpoint checkpoint) throws Exception {
     sock.write("foo");
   }
 
+  @Test
+  public void testSendFileAfterTlsUpgrade() throws Exception {
+    File dir = testFolder.newFolder();
+    int size = 64 * 1024;
+    String content = String.valueOf('a').repeat(size);
+    File f = setupFile(dir.toString(), "upgraded.dat", content);
+    Promise<Void> sent = Promise.promise();
+    server.connectHandler(socket -> {
+      socket.upgradeToSsl(new ServerSSLOptions().setKeyCertOptions(Cert.SERVER_JKS.get()))
+        .compose(v -> socket.sendFile(f.getAbsolutePath()))
+        .onComplete(sent);
+    });
+    server.listen(1234, "localhost").await();
+    NetSocket socket = client.connect(new ConnectOptions()
+      .setPort(1234)
+      .setHost("localhost")
+      .setSsl(true)
+      .setSslOptions(new ClientSSLOptions()
+        .setHostnameVerificationAlgorithm("")
+        .setTrustAll(true))).await();
+    Buffer received = Buffer.buffer();
+    Promise<Void> done = Promise.promise();
+    socket.handler(buff -> {
+      received.appendBuffer(buff);
+      if (received.length() == size) {
+        done.tryComplete();
+      }
+    });
+    sent.future().await();
+    done.future().await();
+    socket.close().await();
+    server.close().await();
+    assertEquals(content, received.toString());
+  }
+
+  @Test
+  public void testSendFileFromClientAfterTlsUpgrade() throws Exception {
+    File dir = testFolder.newFolder();
+    int size = 64 * 1024;
+    String content = String.valueOf('a').repeat(size);
+    File f = setupFile(dir.toString(), "upgraded-client.dat", content);
+    Buffer received = Buffer.buffer();
+    Promise<Void> done = Promise.promise();
+    server.connectHandler(socket -> {
+      socket.upgradeToSsl(new ServerSSLOptions().setKeyCertOptions(Cert.SERVER_JKS.get()))
+        .onSuccess(v -> socket.handler(buff -> {
+          received.appendBuffer(buff);
+          if (received.length() == size) {
+            done.tryComplete();
+          }
+        }));
+    });
+    server.listen(1234, "localhost").await();
+    NetSocket socket = client.connect(1234, "localhost").await();
+    socket.upgradeToSsl(new ClientSSLOptions()
+      .setHostnameVerificationAlgorithm("")
+      .setTrustAll(true)).await();
+    socket.sendFile(f.getAbsolutePath()).await();
+    done.future().await();
+    socket.close().await();
+    server.close().await();
+    assertEquals(content, received.toString());
+  }
+
   @Test
   public void testSendFileDirectory() throws Exception {
     File fDir = testFolder.newFolder();