diff --git a/security-framework/src/secure_transport.rs b/security-framework/src/secure_transport.rs
index f522c713..326a5d32 100644
--- a/security-framework/src/secure_transport.rs
+++ b/security-framework/src/secure_transport.rs
@@ -889,7 +889,15 @@ where S: Write {
     let mut ret = errSecSuccess;
 
     while start < data.len() {
-        match panic::catch_unwind(AssertUnwindSafe(|| conn.stream.write(&data[start..]))) {
+        let write_res = panic::catch_unwind(AssertUnwindSafe(|| {
+            let count = conn.stream.write(&data[start..])?;
+            // Need to flush during the handshake so that the handshake doesn't stall on buffered
+            // write streams. It would be better if we only flushed automatically during the
+            // handshake, and not for the remainder of the stream.
+            conn.stream.flush()?;
+            Ok(count)
+        }));
+        match write_res {
             Ok(Ok(0)) => {
                 ret = errSSLClosedNoNotify;
                 break;
@@ -1449,6 +1457,49 @@ mod test {
         ctx.handshake(stream).expect_err("expected failure");
     }
 
+    #[test]
+    fn connect_buffered_stream() {
+        use std::io::BufWriter;
+
+        /// Small wrapper around a `TcpStream` to provide buffered writes.
+        #[derive(Debug)]
+        struct BufferedTcpStream {
+            reader: TcpStream,
+            writer: BufWriter<TcpStream>,
+        }
+
+        impl BufferedTcpStream {
+            fn new(tcp: TcpStream) -> std::io::Result<Self> {
+                Ok(Self {
+                    writer: BufWriter::with_capacity(500, tcp.try_clone()?),
+                    reader: tcp,
+                })
+            }
+        }
+
+        impl Read for BufferedTcpStream {
+            fn read(&mut self, buf: &mut [u8]) -> std::io::Result<usize> {
+                self.reader.read(buf)
+            }
+        }
+
+        impl Write for BufferedTcpStream {
+            fn write(&mut self, buf: &[u8]) -> std::io::Result<usize> {
+                self.writer.write(buf)
+            }
+
+            fn flush(&mut self) -> std::io::Result<()> {
+                self.writer.flush()
+            }
+        }
+
+        let mut ctx = p!(SslContext::new(SslProtocolSide::CLIENT, SslConnectionType::STREAM));
+        p!(ctx.set_peer_domain_name("google.com"));
+        let stream = p!(TcpStream::connect("google.com:443"));
+        let stream = p!(BufferedTcpStream::new(stream));
+        p!(ctx.handshake(stream));
+    }
+
     #[test]
     fn load_page() {
         let mut ctx = p!(SslContext::new(SslProtocolSide::CLIENT, SslConnectionType::STREAM));