diff --git a/tokio-rustls/Cargo.toml b/tokio-rustls/Cargo.toml
index 5c9f205ca..17a5d9f16 100644
--- a/tokio-rustls/Cargo.toml
+++ b/tokio-rustls/Cargo.toml
@@ -1,6 +1,6 @@
 [package]
 name = "tokio-rustls"
-version = "0.23.2"
+version = "0.23.3"
 authors = ["quininer kel <quininer@live.com>"]
 license = "MIT/Apache-2.0"
 repository = "https://github.com/tokio-rs/tls"
diff --git a/tokio-rustls/src/common/handshake.rs b/tokio-rustls/src/common/handshake.rs
index fcb6dc99a..672527785 100644
--- a/tokio-rustls/src/common/handshake.rs
+++ b/tokio-rustls/src/common/handshake.rs
@@ -62,9 +62,7 @@ where
                 try_poll!(tls_stream.handshake(cx));
             }
 
-            while tls_stream.session.wants_write() {
-                try_poll!(tls_stream.write_io(cx));
-            }
+            try_poll!(Pin::new(&mut tls_stream).poll_flush(cx));
         }
 
         Poll::Ready(Ok(stream))
diff --git a/tokio-rustls/src/common/mod.rs b/tokio-rustls/src/common/mod.rs
index 6de5b979f..fde34c0db 100644
--- a/tokio-rustls/src/common/mod.rs
+++ b/tokio-rustls/src/common/mod.rs
@@ -166,10 +166,14 @@ where
         loop {
             let mut write_would_block = false;
             let mut read_would_block = false;
+            let mut need_flush = false;
 
             while self.session.wants_write() {
                 match self.write_io(cx) {
-                    Poll::Ready(Ok(n)) => wrlen += n,
+                    Poll::Ready(Ok(n)) => {
+                        wrlen += n;
+                        need_flush = true;
+                    }
                     Poll::Pending => {
                         write_would_block = true;
                         break;
@@ -178,6 +182,14 @@ where
                 }
             }
 
+            if need_flush {
+                match Pin::new(&mut self.io).poll_flush(cx) {
+                    Poll::Ready(Ok(())) => (),
+                    Poll::Ready(Err(err)) => return Poll::Ready(Err(err)),
+                    Poll::Pending => write_would_block = true,
+                }
+            }
+
             while !self.eof && self.session.wants_read() {
                 match self.read_io(cx) {
                     Poll::Ready(Ok(0)) => self.eof = true,
diff --git a/tokio-rustls/src/common/test_stream.rs b/tokio-rustls/src/common/test_stream.rs
index 3b3966d49..710a32403 100644
--- a/tokio-rustls/src/common/test_stream.rs
+++ b/tokio-rustls/src/common/test_stream.rs
@@ -202,6 +202,30 @@ async fn stream_handshake() -> io::Result<()> {
     Ok(()) as io::Result<()>
 }
 
+#[tokio::test]
+async fn stream_buffered_handshake() -> io::Result<()> {
+    use tokio::io::BufWriter;
+
+    let (server, mut client) = make_pair();
+    let mut server = Connection::from(server);
+
+    {
+        let mut good = BufWriter::new(Good(&mut server));
+        let mut stream = Stream::new(&mut good, &mut client);
+        let (r, w) = poll_fn(|cx| stream.handshake(cx)).await?;
+
+        assert!(r > 0);
+        assert!(w > 0);
+
+        poll_fn(|cx| stream.handshake(cx)).await?; // finish server handshake
+    }
+
+    assert!(!server.is_handshaking());
+    assert!(!client.is_handshaking());
+
+    Ok(()) as io::Result<()>
+}
+
 #[tokio::test]
 async fn stream_handshake_eof() -> io::Result<()> {
     let (_, mut client) = make_pair();