diff --git a/src/proto/h1/role.rs b/src/proto/h1/role.rs
index 86e9bc95..dd21b623 100644
--- a/src/proto/h1/role.rs
+++ b/src/proto/h1/role.rs
@@ -191,7 +191,9 @@ where
         // This is because Service only allows returning a single Response, and
         // so if you try to reply with a e.g. 100 Continue, you have no way of
         // replying with the latter status code response.
-        let (ret, mut is_last) = if StatusCode::SWITCHING_PROTOCOLS == msg.head.subject {
+        let is_upgrade = msg.head.subject == StatusCode::SWITCHING_PROTOCOLS
+            || (msg.req_method == &Some(Method::CONNECT) && msg.head.subject.is_success());
+        let (ret, mut is_last) = if is_upgrade {
             (T::on_encode_upgrade(&mut msg), true)
         } else if msg.head.subject.is_informational() {
             error!("response with 1xx status code not supported");
@@ -851,12 +853,20 @@ impl OnUpgrade for YesUpgrades {
 
 impl OnUpgrade for NoUpgrades {
     fn on_encode_upgrade(msg: &mut Encode<StatusCode>) -> ::Result<()> {
-        error!("response with 101 status code not supported");
         *msg.head = MessageHead::default();
         msg.head.subject = ::StatusCode::INTERNAL_SERVER_ERROR;
         msg.body = None;
-        //TODO: replace with more descriptive error
-        Err(::Error::new_status())
+
+        if msg.head.subject == StatusCode::SWITCHING_PROTOCOLS {
+            error!("response with 101 status code not supported");
+            Err(Parse::UpgradeNotSupported.into())
+        } else if msg.req_method == &Some(Method::CONNECT) {
+            error!("200 response to CONNECT request not supported");
+            Err(::Error::new_user_unsupported_request_method())
+        } else {
+            debug_assert!(false, "upgrade incorrectly detected");
+            Err(::Error::new_status())
+        }
     }
 
     fn on_decode_upgrade() -> Result<Decoder, Parse> {
@@ -1309,6 +1319,39 @@ mod tests {
         assert_eq!(vec, b"GET / HTTP/1.1\r\nContent-Length: 10\r\nContent-Type: application/json\r\n\r\n".to_vec());
     }
 
+    #[test]
+    fn test_server_no_upgrades_connect_method() {
+        let mut head = MessageHead::default();
+
+        let mut vec = Vec::new();
+        let err = Server::encode(Encode {
+            head: &mut head,
+            body: None,
+            keep_alive: true,
+            req_method: &mut Some(Method::CONNECT),
+            title_case_headers: false,
+        }, &mut vec).unwrap_err();
+
+        assert!(err.is_user());
+        assert_eq!(err.kind(), &::error::Kind::UnsupportedRequestMethod);
+    }
+
+    #[test]
+    fn test_server_yes_upgrades_connect_method() {
+        let mut head = MessageHead::default();
+
+        let mut vec = Vec::new();
+        let encoder = S::<YesUpgrades>::encode(Encode {
+            head: &mut head,
+            body: None,
+            keep_alive: true,
+            req_method: &mut Some(Method::CONNECT),
+            title_case_headers: false,
+        }, &mut vec).unwrap();
+
+        assert!(encoder.is_last());
+    }
+
     #[cfg(feature = "nightly")]
     use test::Bencher;
 
diff --git a/tests/server.rs b/tests/server.rs
index 09c2e9f5..000c7098 100644
--- a/tests/server.rs
+++ b/tests/server.rs
@@ -1147,6 +1147,70 @@ fn upgrades() {
     assert_eq!(vec, b"bar=foo");
 }
 
+#[test]
+fn http_connect() {
+    use tokio_io::io::{read_to_end, write_all};
+    let _ = pretty_env_logger::try_init();
+    let runtime = Runtime::new().unwrap();
+    let listener = tcp_bind(&"127.0.0.1:0".parse().unwrap(), &runtime.reactor()).unwrap();
+    let addr = listener.local_addr().unwrap();
+    let (tx, rx) = oneshot::channel();
+
+    thread::spawn(move || {
+        let mut tcp = connect(&addr);
+        tcp.write_all(b"\
+            CONNECT localhost:80 HTTP/1.1\r\n\
+            \r\n\
+            eagerly optimistic\
+        ").expect("write 1");
+        let mut buf = [0; 256];
+        tcp.read(&mut buf).expect("read 1");
+
+        let expected = "HTTP/1.1 200 OK\r\n";
+        assert_eq!(s(&buf[..expected.len()]), expected);
+        let _ = tx.send(());
+
+        let n = tcp.read(&mut buf).expect("read 2");
+        assert_eq!(s(&buf[..n]), "foo=bar");
+        tcp.write_all(b"bar=foo").expect("write 2");
+    });
+
+    let fut = listener.incoming()
+        .into_future()
+        .map_err(|_| -> hyper::Error { unreachable!() })
+        .and_then(|(item, _incoming)| {
+            let socket = item.unwrap();
+            let conn = Http::new()
+                .serve_connection(socket, service_fn(|_| {
+                    let res = Response::builder()
+                        .status(200)
+                        .body(hyper::Body::empty())
+                        .unwrap();
+                    Ok::<_, hyper::Error>(res)
+                }));
+
+            let mut conn_opt = Some(conn);
+            future::poll_fn(move || {
+                try_ready!(conn_opt.as_mut().unwrap().poll_without_shutdown());
+                // conn is done with HTTP now
+                Ok(conn_opt.take().unwrap().into())
+            })
+        });
+
+    let conn = fut.wait().unwrap();
+
+    // wait so that we don't write until other side saw 101 response
+    rx.wait().unwrap();
+
+    let parts = conn.into_parts();
+    let io = parts.io;
+    assert_eq!(parts.read_buf, "eagerly optimistic");
+
+    let io = write_all(io, b"foo=bar").wait().unwrap().0;
+    let vec = read_to_end(io, vec![]).wait().unwrap().1;
+    assert_eq!(vec, b"bar=foo");
+}
+
 #[test]
 fn parse_errors_send_4xx_response() {
     let runtime = Runtime::new().unwrap();