diff --git a/CHANGES.md b/CHANGES.md
index 45c8117d..6e63848d 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,5 +1,24 @@
 **Experimental**: This is a new format for release notes. The format and availability is subject to change.
 
+## UNRELEASED
+
+### Backward Incompatible Changes
+
+- none
+
+### New Features
+
+- none
+
+### Improvements
+
+- none
+
+### Bug Fixes
+
+- Fixed proxying of websocket requests to avoid possibility of losing initial frames that were sent in the same TCP
+  packet as response headers [#345](https://github.com/cloudflare/cloudflared/issues/345).
+
 ## 2021.3.6
 
 ### Bug Fixes
diff --git a/carrier/websocket.go b/carrier/websocket.go
index 6ae4252b..0bf7cea9 100644
--- a/carrier/websocket.go
+++ b/carrier/websocket.go
@@ -4,6 +4,7 @@ import (
 	"io"
 	"net/http"
 	"net/http/httputil"
+	"net/url"
 
 	"github.com/gorilla/websocket"
 	"github.com/rs/zerolog"
@@ -60,7 +61,7 @@ func createWebsocketStream(options *StartOptions, log *zerolog.Logger) (*cfwebso
 		TLSClientConfig: options.TLSClientConfig,
 		Proxy:           http.ProxyFromEnvironment,
 	}
-	wsConn, resp, err := cfwebsocket.ClientConnect(req, dialer)
+	wsConn, resp, err := clientConnect(req, dialer)
 	defer closeRespBody(resp)
 
 	if err != nil && IsAccessResponse(resp) {
@@ -87,6 +88,63 @@ func createWebsocketStream(options *StartOptions, log *zerolog.Logger) (*cfwebso
 	return &cfwebsocket.GorillaConn{Conn: wsConn}, nil
 }
 
+var stripWebsocketHeaders = []string{
+	"Upgrade",
+	"Connection",
+	"Sec-Websocket-Key",
+	"Sec-Websocket-Version",
+	"Sec-Websocket-Extensions",
+}
+
+// the gorilla websocket library sets its own Upgrade, Connection, Sec-WebSocket-Key,
+// Sec-WebSocket-Version and Sec-Websocket-Extensions headers.
+// https://github.com/gorilla/websocket/blob/master/client.go#L189-L194.
+func websocketHeaders(req *http.Request) http.Header {
+	wsHeaders := make(http.Header)
+	for key, val := range req.Header {
+		wsHeaders[key] = val
+	}
+	// Assume the header keys are in canonical format.
+	for _, header := range stripWebsocketHeaders {
+		wsHeaders.Del(header)
+	}
+	wsHeaders.Set("Host", req.Host) // See TUN-1097
+	return wsHeaders
+}
+
+// clientConnect creates a WebSocket client connection for provided request. Caller is responsible for closing
+// the connection. The response body may not contain the entire response and does
+// not need to be closed by the application.
+func clientConnect(req *http.Request, dialler *websocket.Dialer) (*websocket.Conn, *http.Response, error) {
+	req.URL.Scheme = changeRequestScheme(req.URL)
+	wsHeaders := websocketHeaders(req)
+	if dialler == nil {
+		dialler = &websocket.Dialer{
+			Proxy: http.ProxyFromEnvironment,
+		}
+	}
+	conn, response, err := dialler.Dial(req.URL.String(), wsHeaders)
+	if err != nil {
+		return nil, response, err
+	}
+	return conn, response, nil
+}
+
+// changeRequestScheme is needed as the gorilla websocket library requires the ws scheme.
+// (even though it changes it back to http/https, but ¯\_(ツ)_/¯.)
+func changeRequestScheme(reqURL *url.URL) string {
+	switch reqURL.Scheme {
+	case "https":
+		return "wss"
+	case "http":
+		return "ws"
+	case "":
+		return "ws"
+	default:
+		return reqURL.Scheme
+	}
+}
+
 // createAccessAuthenticatedStream will try load a token from storage and make
 // a connection with the token set on the request. If it still get redirect,
 // this probably means the token in storage is invalid (expired/revoked). If that
@@ -126,7 +184,7 @@ func createAccessWebSocketStream(options *StartOptions, log *zerolog.Logger) (*w
 	dump, err := httputil.DumpRequest(req, false)
 	log.Debug().Msgf("Access Websocket request: %s", string(dump))
 
-	conn, resp, err := cfwebsocket.ClientConnect(req, nil)
+	conn, resp, err := clientConnect(req, nil)
 
 	if resp != nil {
 		r, err := httputil.DumpResponse(resp, true)
diff --git a/carrier/websocket_test.go b/carrier/websocket_test.go
new file mode 100644
index 00000000..a0a32bb8
--- /dev/null
+++ b/carrier/websocket_test.go
@@ -0,0 +1,123 @@
+package carrier
+
+import (
+	"context"
+	"crypto/tls"
+	"crypto/x509"
+	"fmt"
+	"math/rand"
+	"testing"
+	"time"
+
+	gws "github.com/gorilla/websocket"
+	"github.com/rs/zerolog"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"golang.org/x/net/websocket"
+
+	"github.com/cloudflare/cloudflared/hello"
+	"github.com/cloudflare/cloudflared/tlsconfig"
+	cfwebsocket "github.com/cloudflare/cloudflared/websocket"
+)
+
+func websocketClientTLSConfig(t *testing.T) *tls.Config {
+	certPool := x509.NewCertPool()
+	helloCert, err := tlsconfig.GetHelloCertificateX509()
+	assert.NoError(t, err)
+	certPool.AddCert(helloCert)
+	assert.NotNil(t, certPool)
+	return &tls.Config{RootCAs: certPool}
+}
+
+func TestWebsocketHeaders(t *testing.T) {
+	req := testRequest(t, "http://example.com", nil)
+	wsHeaders := websocketHeaders(req)
+	for _, header := range stripWebsocketHeaders {
+		assert.Empty(t, wsHeaders[header])
+	}
+	assert.Equal(t, "curl/7.59.0", wsHeaders.Get("User-Agent"))
+}
+
+func TestServe(t *testing.T) {
+	log := zerolog.Nop()
+	shutdownC := make(chan struct{})
+	errC := make(chan error)
+	listener, err := hello.CreateTLSListener("localhost:1111")
+	assert.NoError(t, err)
+	defer listener.Close()
+
+	go func() {
+		errC <- hello.StartHelloWorldServer(&log, listener, shutdownC)
+	}()
+
+	req := testRequest(t, "https://localhost:1111/ws", nil)
+
+	tlsConfig := websocketClientTLSConfig(t)
+	assert.NotNil(t, tlsConfig)
+	d := gws.Dialer{TLSClientConfig: tlsConfig}
+	conn, resp, err := clientConnect(req, &d)
+	assert.NoError(t, err)
+	assert.Equal(t, "websocket", resp.Header.Get("Upgrade"))
+
+	for i := 0; i < 1000; i++ {
+		messageSize := rand.Int()%2048 + 1
+		clientMessage := make([]byte, messageSize)
+		// rand.Read always returns len(clientMessage) and a nil error
+		rand.Read(clientMessage)
+		err = conn.WriteMessage(websocket.BinaryFrame, clientMessage)
+		assert.NoError(t, err)
+
+		messageType, message, err := conn.ReadMessage()
+		assert.NoError(t, err)
+		assert.Equal(t, websocket.BinaryFrame, messageType)
+		assert.Equal(t, clientMessage, message)
+	}
+
+	_ = conn.Close()
+	close(shutdownC)
+	<-errC
+}
+
+func TestWebsocketWrapper(t *testing.T) {
+	listener, err := hello.CreateTLSListener("localhost:0")
+	require.NoError(t, err)
+
+	serverErrorChan := make(chan error)
+	helloSvrCtx, cancelHelloSvr := context.WithCancel(context.Background())
+	defer func() { <-serverErrorChan }()
+	defer cancelHelloSvr()
+	go func() {
+		log := zerolog.Nop()
+		serverErrorChan <- hello.StartHelloWorldServer(&log, listener, helloSvrCtx.Done())
+	}()
+
+	tlsConfig := websocketClientTLSConfig(t)
+	d := gws.Dialer{TLSClientConfig: tlsConfig, HandshakeTimeout: time.Minute}
+	testAddr := fmt.Sprintf("https://%s/ws", listener.Addr().String())
+	req := testRequest(t, testAddr, nil)
+	conn, resp, err := clientConnect(req, &d)
+	require.NoError(t, err)
+	assert.Equal(t, "websocket", resp.Header.Get("Upgrade"))
+
+	// Websocket now connected to test server so lets check our wrapper
+	wrapper := cfwebsocket.GorillaConn{Conn: conn}
+	buf := make([]byte, 100)
+	wrapper.Write([]byte("abc"))
+	n, err := wrapper.Read(buf)
+	require.NoError(t, err)
+	require.Equal(t, n, 3)
+	require.Equal(t, "abc", string(buf[:n]))
+
+	// Test partial read, read 1 of 3 bytes in one read and the other 2 in another read
+	wrapper.Write([]byte("abc"))
+	buf = buf[:1]
+	n, err = wrapper.Read(buf)
+	require.NoError(t, err)
+	require.Equal(t, n, 1)
+	require.Equal(t, "a", string(buf[:n]))
+	buf = buf[:cap(buf)]
+	n, err = wrapper.Read(buf)
+	require.NoError(t, err)
+	require.Equal(t, n, 2)
+	require.Equal(t, "bc", string(buf[:n]))
+}
diff --git a/ingress/origin_connection.go b/ingress/origin_connection.go
index 3ed17186..c97d42fd 100644
--- a/ingress/origin_connection.go
+++ b/ingress/origin_connection.go
@@ -2,12 +2,9 @@ package ingress
 
 import (
 	"context"
-	"crypto/tls"
 	"io"
 	"net"
-	"net/http"
 
-	gws "github.com/gorilla/websocket"
 	"github.com/rs/zerolog"
 
 	"github.com/cloudflare/cloudflared/ipaccess"
@@ -58,35 +55,6 @@ func (wc *tcpOverWSConnection) Close() {
 	wc.conn.Close()
 }
 
-// wsConnection is an OriginConnection that streams WS between eyeball and origin.
-type wsConnection struct {
-	wsConn *gws.Conn
-	resp   *http.Response
-}
-
-func (wsc *wsConnection) Stream(ctx context.Context, tunnelConn io.ReadWriter, log *zerolog.Logger) {
-	websocket.Stream(tunnelConn, wsc.wsConn.UnderlyingConn(), log)
-}
-
-func (wsc *wsConnection) Close() {
-	wsc.resp.Body.Close()
-	wsc.wsConn.Close()
-}
-
-func newWSConnection(clientTLSConfig *tls.Config, r *http.Request) (OriginConnection, *http.Response, error) {
-	d := &gws.Dialer{
-		TLSClientConfig: clientTLSConfig,
-	}
-	wsConn, resp, err := websocket.ClientConnect(r, d)
-	if err != nil {
-		return nil, nil, err
-	}
-	return &wsConnection{
-		wsConn,
-		resp,
-	}, resp, nil
-}
-
 // socksProxyOverWSConnection is an OriginConnection that streams SOCKS connections over WS.
 // The connection to the origin happens inside the SOCKS code as the client specifies the origin
 // details in the packet.
@@ -100,3 +68,16 @@ func (sp *socksProxyOverWSConnection) Stream(ctx context.Context, tunnelConn io.
 
 func (sp *socksProxyOverWSConnection) Close() {
 }
+
+// wsProxyConnection represents a bidirectional stream for a websocket connection to the origin
+type wsProxyConnection struct {
+	rwc io.ReadWriteCloser
+}
+
+func (conn *wsProxyConnection) Stream(ctx context.Context, tunnelConn io.ReadWriter, log *zerolog.Logger) {
+	websocket.Stream(tunnelConn, conn.rwc, log)
+}
+
+func (conn *wsProxyConnection) Close() {
+	conn.rwc.Close()
+}
diff --git a/ingress/origin_connection_test.go b/ingress/origin_connection_test.go
index 78a2a151..d3294fca 100644
--- a/ingress/origin_connection_test.go
+++ b/ingress/origin_connection_test.go
@@ -3,13 +3,13 @@ package ingress
 import (
 	"bytes"
 	"context"
-	"crypto/tls"
 	"fmt"
 	"io/ioutil"
 	"net"
 	"net/http"
 	"net/http/httptest"
 	"net/url"
+	"sync"
 	"testing"
 	"time"
 
@@ -193,18 +193,26 @@ func TestSocksStreamWSOverTCPConnection(t *testing.T) {
 func TestStreamWSConnection(t *testing.T) {
 	eyeballConn, edgeConn := net.Pipe()
 
-	origin := echoWSOrigin(t)
+	origin := echoWSOrigin(t, true)
 	defer origin.Close()
 
+	var svc httpService
+	err := svc.start(&sync.WaitGroup{}, testLogger, nil, nil, OriginRequestConfig{
+		NoTLSVerify: true,
+	})
+	require.NoError(t, err)
+
 	req, err := http.NewRequest(http.MethodGet, origin.URL, nil)
 	require.NoError(t, err)
 	req.Header.Set("Sec-Websocket-Key", "dGhlIHNhbXBsZSBub25jZQ==")
+	req.Header.Set("Connection", "Upgrade")
+	req.Header.Set("Upgrade", "websocket")
+
+	conn, resp, err := svc.newWebsocketProxyConnection(req)
 
-	clientTLSConfig := &tls.Config{
-		InsecureSkipVerify: true,
-	}
-	wsConn, resp, err := newWSConnection(clientTLSConfig, req)
 	require.NoError(t, err)
+	defer conn.Close()
+
 	require.Equal(t, http.StatusSwitchingProtocols, resp.StatusCode)
 	require.Equal(t, "Upgrade", resp.Header.Get("Connection"))
 	require.Equal(t, "s3pPLMBiTxaQ9kYGzzhZRbK+xOo=", resp.Header.Get("Sec-Websocket-Accept"))
@@ -213,13 +221,37 @@ func TestStreamWSConnection(t *testing.T) {
 	ctx, cancel := context.WithTimeout(context.Background(), testStreamTimeout)
 	defer cancel()
 
+	connClosed := make(chan struct{})
+
 	errGroup, ctx := errgroup.WithContext(ctx)
+	errGroup.Go(func() error {
+		select {
+		case <-connClosed:
+		case <-ctx.Done():
+		}
+		if ctx.Err() == context.DeadlineExceeded {
+			eyeballConn.Close()
+			edgeConn.Close()
+			conn.Close()
+		}
+
+		return ctx.Err()
+	})
+
 	errGroup.Go(func() error {
 		echoWSEyeball(t, eyeballConn)
+		fmt.Println("closing pipe")
+		edgeConn.Close()
+		return eyeballConn.Close()
+	})
+
+	errGroup.Go(func() error {
+		defer conn.Close()
+		conn.Stream(ctx, edgeConn, testLogger)
+		close(connClosed)
 		return nil
 	})
 
-	wsConn.Stream(ctx, edgeConn, testLogger)
 	require.NoError(t, errGroup.Wait())
 }
 
@@ -241,17 +273,23 @@ func (wse *wsEyeball) Write(p []byte) (int, error) {
 }
 
 func echoWSEyeball(t *testing.T, conn net.Conn) {
-	require.NoError(t, wsutil.WriteClientBinary(conn, testMessage))
+	defer func() {
+		assert.NoError(t, conn.Close())
+	}()
+
+	if !assert.NoError(t, wsutil.WriteClientBinary(conn, testMessage)) {
+		return
+	}
 
 	readMsg, err := wsutil.ReadServerBinary(conn)
-	require.NoError(t, err)
+	if !assert.NoError(t, err) {
+		return
+	}
 
-	require.Equal(t, testResponse, readMsg)
-
-	require.NoError(t, conn.Close())
+	assert.Equal(t, testResponse, readMsg)
 }
 
-func echoWSOrigin(t *testing.T) *httptest.Server {
+func echoWSOrigin(t *testing.T, expectMessages bool) *httptest.Server {
 	var upgrader = gorillaWS.Upgrader{
 		ReadBufferSize:  10,
 		WriteBufferSize: 10,
@@ -268,12 +306,17 @@ func echoWSOrigin(t *testing.T) *httptest.Server {
 		require.NoError(t, err)
 		defer conn.Close()
 
+		sawMessage := false
 		for {
 			messageType, p, err := conn.ReadMessage()
 			if err != nil {
+				if expectMessages && !sawMessage {
+					t.Errorf("unexpected error: %v", err)
+				}
 				return
 			}
-			require.Equal(t, testMessage, p)
+			assert.Equal(t, testMessage, p)
+			sawMessage = true
 			if err := conn.WriteMessage(messageType, testResponse); err != nil {
 				return
 			}
diff --git a/ingress/origin_proxy.go b/ingress/origin_proxy.go
index 08ef4bd9..e5956c59 100644
--- a/ingress/origin_proxy.go
+++ b/ingress/origin_proxy.go
@@ -2,8 +2,10 @@ package ingress
 
 import (
 	"fmt"
+	"io"
 	"net"
 	"net/http"
+	"strings"
 
 	"github.com/pkg/errors"
 
@@ -12,7 +14,8 @@ import (
 )
 
 var (
-	switchingProtocolText = fmt.Sprintf("%d %s", http.StatusSwitchingProtocols, http.StatusText(http.StatusSwitchingProtocols))
+	switchingProtocolText        = fmt.Sprintf("%d %s", http.StatusSwitchingProtocols, http.StatusText(http.StatusSwitchingProtocols))
+	errUnsupportedConnectionType = errors.New("internal error: unsupported connection type")
 )
 
 // HTTPOriginProxy can be implemented by origin services that want to proxy http requests.
@@ -42,26 +45,64 @@ func (o *httpService) RoundTrip(req *http.Request) (*http.Response, error) {
 }
 
 func (o *httpService) EstablishConnection(req *http.Request) (OriginConnection, *http.Response, error) {
+	req = req.Clone(req.Context())
+
 	req.URL.Host = o.url.Host
-	req.URL.Scheme = websocket.ChangeRequestScheme(o.url)
+	req.URL.Scheme = o.url.Scheme
+	// allow ws(s) scheme for websocket-only origins, normal http(s) requests will fail
+	switch req.URL.Scheme {
+	case "ws":
+		req.URL.Scheme = "http"
+	case "wss":
+		req.URL.Scheme = "https"
+	}
+
 	if o.hostHeader != "" {
 		// For incoming requests, the Host header is promoted to the Request.Host field and removed from the Header map.
 		req.Host = o.hostHeader
 	}
-	return newWSConnection(o.transport.TLSClientConfig, req)
+
+	return o.newWebsocketProxyConnection(req)
 }
 
-func (o *helloWorld) RoundTrip(req *http.Request) (*http.Response, error) {
-	// Rewrite the request URL so that it goes to the Hello World server.
-	req.URL.Host = o.server.Addr().String()
-	req.URL.Scheme = "https"
-	return o.transport.RoundTrip(req)
-}
+func (o *httpService) newWebsocketProxyConnection(req *http.Request) (OriginConnection, *http.Response, error) {
+	req.Header.Set("Connection", "Upgrade")
+	req.Header.Set("Upgrade", "websocket")
+	req.Header.Set("Sec-WebSocket-Version", "13")
 
-func (o *helloWorld) EstablishConnection(req *http.Request) (OriginConnection, *http.Response, error) {
-	req.URL.Host = o.server.Addr().String()
-	req.URL.Scheme = "wss"
-	return newWSConnection(o.transport.TLSClientConfig, req)
+	req.ContentLength = 0
+	req.Body = nil
+
+	resp, err := o.transport.RoundTrip(req)
+	if err != nil {
+		return nil, nil, err
+	}
+
+	toClose := resp.Body
+	defer func() {
+		if toClose != nil {
+			_ = toClose.Close()
+		}
+	}()
+
+	if resp.StatusCode != http.StatusSwitchingProtocols {
+		return nil, nil, fmt.Errorf("unexpected origin response: %s", resp.Status)
+	}
+	if strings.ToLower(resp.Header.Get("Upgrade")) != "websocket" {
+		return nil, nil, fmt.Errorf("unexpected upgrade: %q", resp.Header.Get("Upgrade"))
+	}
+
+	rwc, ok := resp.Body.(io.ReadWriteCloser)
+	if !ok {
+		return nil, nil, errUnsupportedConnectionType
+	}
+	conn := wsProxyConnection{
+		rwc: rwc,
+	}
+	// clear to prevent defer from closing
+	toClose = nil
+
+	return &conn, resp, nil
 }
 
 func (o *statusCode) RoundTrip(_ *http.Request) (*http.Response, error) {
diff --git a/ingress/origin_proxy_test.go b/ingress/origin_proxy_test.go
index 22266383..4939409f 100644
--- a/ingress/origin_proxy_test.go
+++ b/ingress/origin_proxy_test.go
@@ -33,7 +33,7 @@ func assertEstablishConnectionResponse(t *testing.T,
 }
 
 func TestHTTPServiceEstablishConnection(t *testing.T) {
-	origin := echoWSOrigin(t)
+	origin := echoWSOrigin(t, false)
 	defer origin.Close()
 	originURL, err := url.Parse(origin.URL)
 	require.NoError(t, err)
@@ -71,11 +71,11 @@ func TestHelloWorldEstablishConnection(t *testing.T) {
 	// Scheme and Host of URL will be override by the Scheme and Host of the helloWorld service
 	req, err := http.NewRequest(http.MethodGet, "https://place-holder/ws", nil)
 	require.NoError(t, err)
+	req.Header.Set("Sec-Websocket-Key", "dGhlIHNhbXBsZSBub25jZQ==")
 
 	expectHeader := http.Header{
-		"Connection": {"Upgrade"},
-		// Accept key when Sec-Websocket-Key is not specified
-		"Sec-Websocket-Accept": {"Kfh9QIsMVZcl6xEPYxPHzW8SZ8w="},
+		"Connection":           {"Upgrade"},
+		"Sec-Websocket-Accept": {"s3pPLMBiTxaQ9kYGzzhZRbK+xOo="},
 		"Upgrade":              {"websocket"},
 	}
 	assertEstablishConnectionResponse(t, helloWorldSerivce, req, expectHeader)
diff --git a/ingress/origin_service.go b/ingress/origin_service.go
index eeff7ebc..a915ec72 100644
--- a/ingress/origin_service.go
+++ b/ingress/origin_service.go
@@ -11,7 +11,6 @@ import (
 	"sync"
 	"time"
 
-	gws "github.com/gorilla/websocket"
 	"github.com/pkg/errors"
 	"github.com/rs/zerolog"
 
@@ -19,7 +18,6 @@ import (
 	"github.com/cloudflare/cloudflared/ipaccess"
 	"github.com/cloudflare/cloudflared/socks"
 	"github.com/cloudflare/cloudflared/tlsconfig"
-	"github.com/cloudflare/cloudflared/websocket"
 )
 
 // originService is something a tunnel can proxy traffic to.
@@ -50,16 +48,6 @@ func (o *unixSocketPath) start(wg *sync.WaitGroup, log *zerolog.Logger, shutdown
 	return nil
 }
 
-func (o *unixSocketPath) Dial(reqURL *url.URL, headers http.Header) (*gws.Conn, *http.Response, error) {
-	d := &gws.Dialer{
-		NetDial:         o.transport.Dial,
-		NetDialContext:  o.transport.DialContext,
-		TLSClientConfig: o.transport.TLSClientConfig,
-	}
-	reqURL.Scheme = websocket.ChangeRequestScheme(reqURL)
-	return d.Dial(reqURL.String(), headers)
-}
-
 type httpService struct {
 	url        *url.URL
 	hostHeader string
@@ -171,8 +159,8 @@ func (o *socksProxyOverWSService) String() string {
 // HelloWorld is an OriginService for the built-in Hello World server.
 // Users only use this for testing and experimenting with cloudflared.
 type helloWorld struct {
-	server    net.Listener
-	transport *http.Transport
+	httpService
+	server net.Listener
 }
 
 func (o *helloWorld) String() string {
@@ -187,11 +175,10 @@ func (o *helloWorld) start(
 	errC chan error,
 	cfg OriginRequestConfig,
 ) error {
-	transport, err := newHTTPTransport(o, cfg, log)
-	if err != nil {
+	if err := o.httpService.start(wg, log, shutdownC, errC, cfg); err != nil {
 		return err
 	}
-	o.transport = transport
+
 	helloListener, err := hello.CreateTLSListener("127.0.0.1:")
 	if err != nil {
 		return errors.Wrap(err, "Cannot start Hello World Server")
@@ -202,6 +189,12 @@ func (o *helloWorld) start(
 		_ = hello.StartHelloWorldServer(log, helloListener, shutdownC)
 	}()
 	o.server = helloListener
+
+	o.httpService.url = &url.URL{
+		Scheme: "https",
+		Host:   o.server.Addr().String(),
+	}
+
 	return nil
 }
 
diff --git a/origin/proxy.go b/origin/proxy.go
index 0e114ab0..87f77b3a 100644
--- a/origin/proxy.go
+++ b/origin/proxy.go
@@ -67,7 +67,7 @@ func (p *proxy) Proxy(w connection.ResponseWriter, req *http.Request, sourceConn
 			lbProbe: lbProbe,
 			rule:    ingress.ServiceWarpRouting,
 		}
-		if err := p.proxyStreamRequest(serveCtx, w, req, sourceConnectionType, p.warpRouting.Proxy, logFields); err != nil {
+		if err := p.proxyStreamRequest(serveCtx, w, req, p.warpRouting.Proxy, logFields); err != nil {
 			p.logRequestError(err, cfRay, ingress.ServiceWarpRouting)
 			return err
 		}
@@ -96,7 +96,7 @@ func (p *proxy) Proxy(w connection.ResponseWriter, req *http.Request, sourceConn
 		return fmt.Errorf("Not a connection-oriented service")
 	}
 
-	if err := p.proxyStreamRequest(serveCtx, w, req, sourceConnectionType, connectionProxy, logFields); err != nil {
+	if err := p.proxyStreamRequest(serveCtx, w, req, connectionProxy, logFields); err != nil {
 		p.logRequestError(err, cfRay, ruleNum)
 		return err
 	}
@@ -152,7 +152,6 @@ func (p *proxy) proxyStreamRequest(
 	serveCtx context.Context,
 	w connection.ResponseWriter,
 	req *http.Request,
-	sourceConnectionType connection.Type,
 	connectionProxy ingress.StreamBasedOriginProxy,
 	fields logFields,
 ) error {
diff --git a/origin/proxy_test.go b/origin/proxy_test.go
index dc4bdbe4..1af9add4 100644
--- a/origin/proxy_test.go
+++ b/origin/proxy_test.go
@@ -19,6 +19,7 @@ import (
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"github.com/urfave/cli/v2"
+	"golang.org/x/sync/errgroup"
 
 	"github.com/cloudflare/cloudflared/config"
 	"github.com/cloudflare/cloudflared/connection"
@@ -79,6 +80,11 @@ func (w *mockWSRespWriter) respBody() io.ReadWriter {
 	return bytes.NewBuffer(data)
 }
 
+func (w *mockWSRespWriter) Close() error {
+	close(w.writeNotification)
+	return nil
+}
+
 func (w *mockWSRespWriter) Read(data []byte) (int, error) {
 	return w.reader.Read(data)
 }
@@ -125,14 +131,14 @@ func TestProxySingleOrigin(t *testing.T) {
 	require.NoError(t, ingressRule.StartOrigins(&wg, &log, ctx.Done(), errC))
 
 	proxy := NewOriginProxy(ingressRule, unusedWarpRoutingService, testTags, &log)
-	t.Run("testProxyHTTP", testProxyHTTP(t, proxy))
-	t.Run("testProxyWebsocket", testProxyWebsocket(t, proxy))
-	t.Run("testProxySSE", testProxySSE(t, proxy))
+	t.Run("testProxyHTTP", testProxyHTTP(proxy))
+	t.Run("testProxyWebsocket", testProxyWebsocket(proxy))
+	t.Run("testProxySSE", testProxySSE(proxy))
 	cancel()
 	wg.Wait()
 }
 
-func testProxyHTTP(t *testing.T, proxy connection.OriginProxy) func(t *testing.T) {
+func testProxyHTTP(proxy connection.OriginProxy) func(t *testing.T) {
 	return func(t *testing.T) {
 		responseWriter := newMockHTTPRespWriter()
 		req, err := http.NewRequest(http.MethodGet, "http://localhost:8080", nil)
@@ -145,23 +151,43 @@ func testProxyHTTP(t *testing.T, proxy connection.OriginProxy) func(t *testing.T
 	}
 }
 
-func testProxyWebsocket(t *testing.T, proxy connection.OriginProxy) func(t *testing.T) {
+func testProxyWebsocket(proxy connection.OriginProxy) func(t *testing.T) {
 	return func(t *testing.T) {
 		// WSRoute is a websocket echo handler
-		ctx, cancel := context.WithCancel(context.Background())
+		const testTimeout = 5 * time.Second * 1000
+		ctx, cancel := context.WithTimeout(context.Background(), testTimeout)
+		defer cancel()
 		readPipe, writePipe := io.Pipe()
 		req, err := http.NewRequestWithContext(ctx, http.MethodGet, fmt.Sprintf("http://localhost:8080%s", hello.WSRoute), readPipe)
-		responseWriter := newMockWSRespWriter(readPipe)
+		req.Header.Set("Sec-Websocket-Key", "dGhlIHNhbXBsZSBub25jZQ==")
+		req.Header.Set("Connection", "Upgrade")
+		req.Header.Set("Upgrade", "websocket")
+		responseWriter := newMockWSRespWriter(nil)
 
-		var wg sync.WaitGroup
-		wg.Add(1)
-		go func() {
-			defer wg.Done()
+		finished := make(chan struct{})
+
+		errGroup, ctx := errgroup.WithContext(ctx)
+		errGroup.Go(func() error {
 			err = proxy.Proxy(responseWriter, req, connection.TypeWebsocket)
 			require.NoError(t, err)
 
 			require.Equal(t, http.StatusSwitchingProtocols, responseWriter.Code)
-		}()
+			return nil
+		})
+
+		errGroup.Go(func() error {
+			select {
+			case <-finished:
+			case <-ctx.Done():
+			}
+			if ctx.Err() == context.DeadlineExceeded {
+				t.Errorf("Test timed out")
+				readPipe.Close()
+				writePipe.Close()
+				responseWriter.Close()
+			}
+			return nil
+		})
 
 		msg := []byte("test websocket")
 		err = wsutil.WriteClientText(writePipe, msg)
@@ -179,12 +205,16 @@ func testProxyWebsocket(t *testing.T, proxy connection.OriginProxy) func(t *test
 		require.NoError(t, err)
 		require.Equal(t, msg, returnedMsg)
 
-		cancel()
-		wg.Wait()
+		_ = readPipe.Close()
+		_ = writePipe.Close()
+		_ = responseWriter.Close()
+
+		close(finished)
+		errGroup.Wait()
 	}
 }
 
-func testProxySSE(t *testing.T, proxy connection.OriginProxy) func(t *testing.T) {
+func testProxySSE(proxy connection.OriginProxy) func(t *testing.T) {
 	return func(t *testing.T) {
 		var (
 			pushCount = 50
diff --git a/websocket/websocket.go b/websocket/websocket.go
index 6a619b70..b94b4f54 100644
--- a/websocket/websocket.go
+++ b/websocket/websocket.go
@@ -3,116 +3,47 @@ package websocket
 import (
 	"crypto/sha1"
 	"encoding/base64"
+	"encoding/hex"
+	"errors"
+	"fmt"
 	"io"
 	"net/http"
-	"net/url"
+	"time"
 
 	"github.com/gorilla/websocket"
 	"github.com/rs/zerolog"
 )
 
-var stripWebsocketHeaders = []string{
-	"Upgrade",
-	"Connection",
-	"Sec-Websocket-Key",
-	"Sec-Websocket-Version",
-	"Sec-Websocket-Extensions",
-}
-
 // IsWebSocketUpgrade checks to see if the request is a WebSocket connection.
 func IsWebSocketUpgrade(req *http.Request) bool {
 	return websocket.IsWebSocketUpgrade(req)
 }
 
-// ClientConnect creates a WebSocket client connection for provided request. Caller is responsible for closing
-// the connection. The response body may not contain the entire response and does
-// not need to be closed by the application.
-func ClientConnect(req *http.Request, dialler *websocket.Dialer) (*websocket.Conn, *http.Response, error) {
-	req.URL.Scheme = ChangeRequestScheme(req.URL)
-	wsHeaders := websocketHeaders(req)
-	if dialler == nil {
-		dialler = &websocket.Dialer{
-			Proxy: http.ProxyFromEnvironment,
-		}
-	}
-	conn, response, err := dialler.Dial(req.URL.String(), wsHeaders)
-	if err != nil {
-		return nil, response, err
-	}
-	response.Header.Set("Sec-WebSocket-Accept", generateAcceptKey(req))
-	return conn, response, nil
-}
-
 // NewResponseHeader returns headers needed to return to origin for completing handshake
 func NewResponseHeader(req *http.Request) http.Header {
 	header := http.Header{}
 	header.Add("Connection", "Upgrade")
-	header.Add("Sec-Websocket-Accept", generateAcceptKey(req))
+	header.Add("Sec-Websocket-Accept", generateAcceptKey(req.Header.Get("Sec-WebSocket-Key")))
 	header.Add("Upgrade", "websocket")
 	return header
 }
 
-// the gorilla websocket library sets its own Upgrade, Connection, Sec-WebSocket-Key,
-// Sec-WebSocket-Version and Sec-Websocket-Extensions headers.
-// https://github.com/gorilla/websocket/blob/master/client.go#L189-L194.
-func websocketHeaders(req *http.Request) http.Header {
-	wsHeaders := make(http.Header)
-	for key, val := range req.Header {
-		wsHeaders[key] = val
-	}
-	// Assume the header keys are in canonical format.
-	for _, header := range stripWebsocketHeaders {
-		wsHeaders.Del(header)
-	}
-	wsHeaders.Set("Host", req.Host) // See TUN-1097
-	return wsHeaders
-}
-
-// sha1Base64 sha1 and then base64 encodes str.
-func sha1Base64(str string) string {
-	hasher := sha1.New()
-	_, _ = io.WriteString(hasher, str)
-	hash := hasher.Sum(nil)
-	return base64.StdEncoding.EncodeToString(hash)
-}
-
-// generateAcceptKey returns the string needed for the Sec-WebSocket-Accept header.
-// https://tools.ietf.org/html/rfc6455#section-1.3 describes this process in more detail.
-func generateAcceptKey(req *http.Request) string {
-	return sha1Base64(req.Header.Get("Sec-WebSocket-Key") + "258EAFA5-E914-47DA-95CA-C5AB0DC85B11")
-}
-
-// ChangeRequestScheme is needed as the gorilla websocket library requires the ws scheme.
-// (even though it changes it back to http/https, but ¯\_(ツ)_/¯.)
-func ChangeRequestScheme(reqURL *url.URL) string {
-	switch reqURL.Scheme {
-	case "https":
-		return "wss"
-	case "http":
-		return "ws"
-	case "":
-		return "ws"
-	default:
-		return reqURL.Scheme
-	}
-}
-
 // Stream copies copy data to & from provided io.ReadWriters.
-func Stream(conn, backendConn io.ReadWriter, log *zerolog.Logger) {
+func Stream(tunnelConn, originConn io.ReadWriter, log *zerolog.Logger) {
 	proxyDone := make(chan struct{}, 2)
 
 	go func() {
-		_, err := io.Copy(conn, backendConn)
+		_, err := copyData(tunnelConn, originConn, "origin->tunnel")
 		if err != nil {
-			log.Debug().Msgf("conn to backendConn copy: %v", err)
+			log.Debug().Msgf("origin to tunnel copy: %v", err)
 		}
 		proxyDone <- struct{}{}
 	}()
 
 	go func() {
-		_, err := io.Copy(backendConn, conn)
+		_, err := copyData(originConn, tunnelConn, "tunnel->origin")
 		if err != nil {
-			log.Debug().Msgf("backendConn to conn copy: %v", err)
+			log.Debug().Msgf("tunnel to origin copy: %v", err)
 		}
 		proxyDone <- struct{}{}
 	}()
@@ -120,3 +51,60 @@ func Stream(conn, backendConn io.ReadWriter, log *zerolog.Logger) {
 	// If one side is done, we are done.
 	<-proxyDone
 }
+
+// when set to true, enables logging of content copied to/from origin and tunnel
+const debugCopy = false
+
+func copyData(dst io.Writer, src io.Reader, dir string) (written int64, err error) {
+	if debugCopy {
+		// copyBuffer is based on stdio Copy implementation but shows copied data
+		copyBuffer := func(dst io.Writer, src io.Reader, dir string) (written int64, err error) {
+			var buf []byte
+			size := 32 * 1024
+			buf = make([]byte, size)
+			for {
+				t := time.Now()
+				nr, er := src.Read(buf)
+				if nr > 0 {
+					fmt.Println(dir, t.UnixNano(), "\n"+hex.Dump(buf[0:nr]))
+					nw, ew := dst.Write(buf[0:nr])
+					if nw < 0 || nr < nw {
+						nw = 0
+						if ew == nil {
+							ew = errors.New("invalid write")
+						}
+					}
+					written += int64(nw)
+					if ew != nil {
+						err = ew
+						break
+					}
+					if nr != nw {
+						err = io.ErrShortWrite
+						break
+					}
+				}
+				if er != nil {
+					if er != io.EOF {
+						err = er
+					}
+					break
+				}
+			}
+			return written, err
+		}
+		return copyBuffer(dst, src, dir)
+	} else {
+		return io.Copy(dst, src)
+	}
+}
+
+// from RFC-6455
+var keyGUID = []byte("258EAFA5-E914-47DA-95CA-C5AB0DC85B11")
+
+func generateAcceptKey(challengeKey string) string {
+	h := sha1.New()
+	h.Write([]byte(challengeKey))
+	h.Write(keyGUID)
+	return base64.StdEncoding.EncodeToString(h.Sum(nil))
+}
diff --git a/websocket/websocket_test.go b/websocket/websocket_test.go
index e738a106..5d661a88 100644
--- a/websocket/websocket_test.go
+++ b/websocket/websocket_test.go
@@ -1,24 +1,9 @@
 package websocket
 
 import (
-	"context"
-	"crypto/tls"
-	"crypto/x509"
-	"fmt"
-	"io"
-	"math/rand"
-	"net/http"
 	"testing"
-	"time"
 
-	gws "github.com/gorilla/websocket"
-	"github.com/rs/zerolog"
 	"github.com/stretchr/testify/assert"
-	"github.com/stretchr/testify/require"
-	"golang.org/x/net/websocket"
-
-	"github.com/cloudflare/cloudflared/hello"
-	"github.com/cloudflare/cloudflared/tlsconfig"
 )
 
 const (
@@ -28,126 +13,6 @@ const (
 	testSecWebsocketAccept = "s3pPLMBiTxaQ9kYGzzhZRbK+xOo="
 )
 
-func testRequest(t *testing.T, url string, stream io.ReadWriter) *http.Request {
-	req, err := http.NewRequest("GET", url, stream)
-	if err != nil {
-		t.Fatalf("testRequestHeader error")
-	}
-
-	req.Header.Add("Connection", "Upgrade")
-	req.Header.Add("Upgrade", "WebSocket")
-	req.Header.Add("Sec-Websocket-Key", testSecWebsocketKey)
-	req.Header.Add("Sec-Websocket-Protocol", "tunnel-protocol")
-	req.Header.Add("Sec-Websocket-Version", "13")
-	req.Header.Add("User-Agent", "curl/7.59.0")
-
-	return req
-}
-
-func websocketClientTLSConfig(t *testing.T) *tls.Config {
-	certPool := x509.NewCertPool()
-	helloCert, err := tlsconfig.GetHelloCertificateX509()
-	assert.NoError(t, err)
-	certPool.AddCert(helloCert)
-	assert.NotNil(t, certPool)
-	return &tls.Config{RootCAs: certPool}
-}
-
-func TestWebsocketHeaders(t *testing.T) {
-	req := testRequest(t, "http://example.com", nil)
-	wsHeaders := websocketHeaders(req)
-	for _, header := range stripWebsocketHeaders {
-		assert.Empty(t, wsHeaders[header])
-	}
-	assert.Equal(t, "curl/7.59.0", wsHeaders.Get("User-Agent"))
-}
-
 func TestGenerateAcceptKey(t *testing.T) {
-	req := testRequest(t, "http://example.com", nil)
-	assert.Equal(t, testSecWebsocketAccept, generateAcceptKey(req))
-}
-
-func TestServe(t *testing.T) {
-	log := zerolog.Nop()
-	shutdownC := make(chan struct{})
-	errC := make(chan error)
-	listener, err := hello.CreateTLSListener("localhost:1111")
-	assert.NoError(t, err)
-	defer listener.Close()
-
-	go func() {
-		errC <- hello.StartHelloWorldServer(&log, listener, shutdownC)
-	}()
-
-	req := testRequest(t, "https://localhost:1111/ws", nil)
-
-	tlsConfig := websocketClientTLSConfig(t)
-	assert.NotNil(t, tlsConfig)
-	d := gws.Dialer{TLSClientConfig: tlsConfig}
-	conn, resp, err := ClientConnect(req, &d)
-	assert.NoError(t, err)
-	assert.Equal(t, testSecWebsocketAccept, resp.Header.Get("Sec-WebSocket-Accept"))
-
-	for i := 0; i < 1000; i++ {
-		messageSize := rand.Int()%2048 + 1
-		clientMessage := make([]byte, messageSize)
-		// rand.Read always returns len(clientMessage) and a nil error
-		rand.Read(clientMessage)
-		err = conn.WriteMessage(websocket.BinaryFrame, clientMessage)
-		assert.NoError(t, err)
-
-		messageType, message, err := conn.ReadMessage()
-		assert.NoError(t, err)
-		assert.Equal(t, websocket.BinaryFrame, messageType)
-		assert.Equal(t, clientMessage, message)
-	}
-
-	_ = conn.Close()
-	close(shutdownC)
-	<-errC
-}
-
-func TestWebsocketWrapper(t *testing.T) {
-
-	listener, err := hello.CreateTLSListener("localhost:0")
-	require.NoError(t, err)
-
-	serverErrorChan := make(chan error)
-	helloSvrCtx, cancelHelloSvr := context.WithCancel(context.Background())
-	defer func() { <-serverErrorChan }()
-	defer cancelHelloSvr()
-	go func() {
-		log := zerolog.Nop()
-		serverErrorChan <- hello.StartHelloWorldServer(&log, listener, helloSvrCtx.Done())
-	}()
-
-	tlsConfig := websocketClientTLSConfig(t)
-	d := gws.Dialer{TLSClientConfig: tlsConfig, HandshakeTimeout: time.Minute}
-	testAddr := fmt.Sprintf("https://%s/ws", listener.Addr().String())
-	req := testRequest(t, testAddr, nil)
-	conn, resp, err := ClientConnect(req, &d)
-	require.NoError(t, err)
-	require.Equal(t, testSecWebsocketAccept, resp.Header.Get("Sec-WebSocket-Accept"))
-
-	// Websocket now connected to test server so lets check our wrapper
-	wrapper := GorillaConn{Conn: conn}
-	buf := make([]byte, 100)
-	wrapper.Write([]byte("abc"))
-	n, err := wrapper.Read(buf)
-	require.NoError(t, err)
-	require.Equal(t, n, 3)
-	require.Equal(t, "abc", string(buf[:n]))
-
-	// Test partial read, read 1 of 3 bytes in one read and the other 2 in another read
-	wrapper.Write([]byte("abc"))
-	buf = buf[:1]
-	n, err = wrapper.Read(buf)
-	require.NoError(t, err)
-	require.Equal(t, n, 1)
-	require.Equal(t, "a", string(buf[:n]))
-	buf = buf[:cap(buf)]
-	n, err = wrapper.Read(buf)
-	require.NoError(t, err)
-	require.Equal(t, n, 2)
-	require.Equal(t, "bc", string(buf[:n]))
+	assert.Equal(t, testSecWebsocketAccept, generateAcceptKey(testSecWebsocketKey))
 }