diff --git a/orchestration/orchestrator_test.go b/orchestration/orchestrator_test.go
index f3638ea7..5afcb8d9 100644
--- a/orchestration/orchestrator_test.go
+++ b/orchestration/orchestrator_test.go
@@ -249,7 +249,10 @@ func TestConcurrentUpdateAndRead(t *testing.T) {
 		}
 	)
 
-	orchestrator, err := NewOrchestrator(context.Background(), initConfig, testTags, &testLogger)
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	orchestrator, err := NewOrchestrator(ctx, initConfig, testTags, &testLogger)
 	require.NoError(t, err)
 
 	updateWithValidation(t, orchestrator, 1, configJSONV1)
@@ -265,8 +268,9 @@ func TestConcurrentUpdateAndRead(t *testing.T) {
 		wg.Add(1)
 		go func(i int, originProxy connection.OriginProxy) {
 			defer wg.Done()
-			resp, err := proxyHTTP(t, originProxy, hostname)
-			require.NoError(t, err)
+			resp, err := proxyHTTP(originProxy, hostname)
+			require.NoError(t, err, "proxyHTTP %d failed %v", i, err)
+			defer resp.Body.Close()
 
 			var warpRoutingDisabled bool
 			// The response can be from initOrigin, http_status:204 or http_status:418
@@ -290,7 +294,7 @@ func TestConcurrentUpdateAndRead(t *testing.T) {
 			// Once we have originProxy, it won't be changed by configuration updates.
 			// We can infer the version by the ProxyHTTP response code
 			pr, pw := io.Pipe()
-			// concurrentRespWriter makes sure ResponseRecorder is not read/write concurrently, and read waits for the first write
+
 			w := newRespReadWriteFlusher()
 
 			// Write TCP message and make sure it's echo back. This has to be done in a go routune since ProxyTCP doesn't
@@ -303,7 +307,14 @@ func TestConcurrentUpdateAndRead(t *testing.T) {
 					tcpEyeball(t, pw, tcpBody, w)
 				}()
 			}
-			proxyTCP(t, originProxy, tcpOrigin.Addr().String(), w, pr, warpRoutingDisabled)
+
+			err = proxyTCP(ctx, originProxy, tcpOrigin.Addr().String(), w, pr)
+			if warpRoutingDisabled {
+				require.Error(t, err, "expect proxyTCP %d to return error", i)
+			} else {
+				require.NoError(t, err, "proxyTCP %d failed %v", i, err)
+			}
+
 		}(i, originProxy)
 
 		if i == concurrentRequests/4 {
@@ -319,6 +330,7 @@ func TestConcurrentUpdateAndRead(t *testing.T) {
 			wg.Add(1)
 			go func() {
 				defer wg.Done()
+				// Makes sure v2 is applied before v3
 				<-appliedV2
 				updateWithValidation(t, orchestrator, 3, configJSONV3)
 			}()
@@ -328,14 +340,18 @@ func TestConcurrentUpdateAndRead(t *testing.T) {
 	wg.Wait()
 }
 
-func proxyHTTP(t *testing.T, originProxy connection.OriginProxy, hostname string) (*http.Response, error) {
+func proxyHTTP(originProxy connection.OriginProxy, hostname string) (*http.Response, error) {
 	req, err := http.NewRequest(http.MethodGet, fmt.Sprintf("http://%s", hostname), nil)
-	require.NoError(t, err)
+	if err != nil {
+		return nil, err
+	}
 
 	w := httptest.NewRecorder()
 	log := zerolog.Nop()
 	respWriter, err := connection.NewHTTP2RespWriter(req, w, connection.TypeHTTP, &log)
-	require.NoError(t, err)
+	if err != nil {
+		return nil, err
+	}
 
 	err = originProxy.ProxyHTTP(respWriter, req, false)
 	if err != nil {
@@ -356,13 +372,17 @@ func tcpEyeball(t *testing.T, reqWriter io.WriteCloser, body string, respReadWri
 	require.Equal(t, writeN, n)
 }
 
-func proxyTCP(t *testing.T, originProxy connection.OriginProxy, originAddr string, w http.ResponseWriter, reqBody io.ReadCloser, expectErr bool) {
+func proxyTCP(ctx context.Context, originProxy connection.OriginProxy, originAddr string, w http.ResponseWriter, reqBody io.ReadCloser) error {
 	req, err := http.NewRequest(http.MethodGet, fmt.Sprintf("http://%s", originAddr), reqBody)
-	require.NoError(t, err)
+	if err != nil {
+		return err
+	}
 
 	log := zerolog.Nop()
 	respWriter, err := connection.NewHTTP2RespWriter(req, w, connection.TypeTCP, &log)
-	require.NoError(t, err)
+	if err != nil {
+		return err
+	}
 
 	tcpReq := &connection.TCPRequest{
 		Dest:    originAddr,
@@ -370,12 +390,8 @@ func proxyTCP(t *testing.T, originProxy connection.OriginProxy, originAddr strin
 		LBProbe: false,
 	}
 	rws := connection.NewHTTPResponseReadWriterAcker(respWriter, req)
-	if expectErr {
-		require.Error(t, originProxy.ProxyTCP(context.Background(), rws, tcpReq))
-		return
-	}
 
-	require.NoError(t, originProxy.ProxyTCP(context.Background(), rws, tcpReq))
+	return originProxy.ProxyTCP(ctx, rws, tcpReq)
 }
 
 func serveTCPOrigin(t *testing.T, tcpOrigin net.Listener, wg *sync.WaitGroup) {
@@ -471,7 +487,7 @@ func TestClosePreviousProxies(t *testing.T) {
 
 	originProxyV1, err := orchestrator.GetOriginProxy()
 	require.NoError(t, err)
-	resp, err := proxyHTTP(t, originProxyV1, hostname)
+	resp, err := proxyHTTP(originProxyV1, hostname)
 	require.NoError(t, err)
 	require.Equal(t, http.StatusOK, resp.StatusCode)
 
@@ -479,12 +495,12 @@ func TestClosePreviousProxies(t *testing.T) {
 
 	originProxyV2, err := orchestrator.GetOriginProxy()
 	require.NoError(t, err)
-	resp, err = proxyHTTP(t, originProxyV2, hostname)
+	resp, err = proxyHTTP(originProxyV2, hostname)
 	require.NoError(t, err)
 	require.Equal(t, http.StatusTeapot, resp.StatusCode)
 
 	// The hello-world server in config v1 should have been stopped
-	resp, err = proxyHTTP(t, originProxyV1, hostname)
+	resp, err = proxyHTTP(originProxyV1, hostname)
 	require.Error(t, err)
 	require.Nil(t, resp)
 
@@ -495,7 +511,7 @@ func TestClosePreviousProxies(t *testing.T) {
 	require.NoError(t, err)
 	require.NotEqual(t, originProxyV1, originProxyV3)
 
-	resp, err = proxyHTTP(t, originProxyV3, hostname)
+	resp, err = proxyHTTP(originProxyV3, hostname)
 	require.NoError(t, err)
 	require.Equal(t, http.StatusOK, resp.StatusCode)
 
@@ -504,7 +520,7 @@ func TestClosePreviousProxies(t *testing.T) {
 	// Wait for proxies to shutdown
 	time.Sleep(time.Millisecond * 10)
 
-	resp, err = proxyHTTP(t, originProxyV3, hostname)
+	resp, err = proxyHTTP(originProxyV3, hostname)
 	require.Error(t, err)
 	require.Nil(t, resp)
 }
@@ -553,6 +569,9 @@ func TestPersistentConnection(t *testing.T) {
 	tcpReqReader, tcpReqWriter := io.Pipe()
 	tcpRespReadWriter := newRespReadWriteFlusher()
 
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
 	var wg sync.WaitGroup
 	wg.Add(3)
 	// Start TCP origin
@@ -570,7 +589,7 @@ func TestPersistentConnection(t *testing.T) {
 	// Simulate cloudflared recieving a TCP connection
 	go func() {
 		defer wg.Done()
-		proxyTCP(t, originProxy, tcpOrigin.Addr().String(), tcpRespReadWriter, tcpReqReader, false)
+		require.NoError(t, proxyTCP(ctx, originProxy, tcpOrigin.Addr().String(), tcpRespReadWriter, tcpReqReader))
 	}()
 	// Simulate cloudflared recieving a WS connection
 	go func() {