From 976df53bdc4adae055be7ec6b516e79b310d24b6 Mon Sep 17 00:00:00 2001
From: Colin Adler <colin1adler@gmail.com>
Date: Fri, 10 Jun 2022 17:57:52 -0500
Subject: [PATCH 1/2] fix(devtunnel): close `http.Server` before wireguard
 interface

---
 coderd/devtunnel/tunnel.go      | 26 ++++++++++++++++++--------
 coderd/devtunnel/tunnel_test.go | 16 +++++++++++++++-
 2 files changed, 33 insertions(+), 9 deletions(-)

diff --git a/coderd/devtunnel/tunnel.go b/coderd/devtunnel/tunnel.go
index ea15c7406f07c..092cdd52ee5f6 100644
--- a/coderd/devtunnel/tunnel.go
+++ b/coderd/devtunnel/tunnel.go
@@ -51,7 +51,7 @@ type configExt struct {
 
 // NewWithConfig calls New with the given config. For documentation, see New.
 func NewWithConfig(ctx context.Context, logger slog.Logger, cfg Config) (*Tunnel, <-chan error, error) {
-	err := startUpdateRoutine(ctx, logger, cfg)
+	routineEnd, err := startUpdateRoutine(ctx, logger, cfg)
 	if err != nil {
 		return nil, nil, xerrors.Errorf("start update routine: %w", err)
 	}
@@ -101,6 +101,7 @@ allowed_ip=%s/128`,
 		case <-ctx.Done():
 			_ = wgListen.Close()
 			dev.Close()
+			<-routineEnd
 			close(ch)
 
 		case <-dev.Wait():
@@ -128,21 +129,24 @@ func New(ctx context.Context, logger slog.Logger) (*Tunnel, <-chan error, error)
 	return NewWithConfig(ctx, logger, cfg)
 }
 
-func startUpdateRoutine(ctx context.Context, logger slog.Logger, cfg Config) error {
+func startUpdateRoutine(ctx context.Context, logger slog.Logger, cfg Config) (<-chan struct{}, error) {
 	// Ensure we send the first config before spawning in the background.
 	_, err := sendConfigToServer(ctx, cfg)
 	if err != nil {
-		return xerrors.Errorf("send config to server: %w", err)
+		return nil, xerrors.Errorf("send config to server: %w", err)
 	}
 
+	endCh := make(chan struct{})
 	go func() {
+		defer close(endCh)
 		ticker := time.NewTicker(30 * time.Second)
 		defer ticker.Stop()
 
 		for {
 			select {
 			case <-ctx.Done():
-				break
+				return
+
 			case <-ticker.C:
 			}
 
@@ -152,19 +156,25 @@ func startUpdateRoutine(ctx context.Context, logger slog.Logger, cfg Config) err
 			}
 		}
 	}()
-	return nil
+	return endCh, nil
 }
 
-func sendConfigToServer(_ context.Context, cfg Config) (created bool, err error) {
+func sendConfigToServer(ctx context.Context, cfg Config) (created bool, err error) {
 	raw, err := json.Marshal(configExt(cfg))
 	if err != nil {
 		return false, xerrors.Errorf("marshal config: %w", err)
 	}
 
-	res, err := http.Post("https://"+EndpointHTTPS+"/tun", "application/json", bytes.NewReader(raw))
+	req, err := http.NewRequestWithContext(ctx, "POST", "https://"+EndpointHTTPS+"/tun", bytes.NewReader(raw))
+	if err != nil {
+		return false, xerrors.Errorf("new request: %w", err)
+	}
+
+	res, err := http.DefaultClient.Do(req)
 	if err != nil {
-		return false, xerrors.Errorf("send request: %w", err)
+		return false, xerrors.Errorf("do request: %w", err)
 	}
+
 	_, _ = io.Copy(io.Discard, res.Body)
 	_ = res.Body.Close()
 
diff --git a/coderd/devtunnel/tunnel_test.go b/coderd/devtunnel/tunnel_test.go
index 30e3d5fc94851..9b549cabb1063 100644
--- a/coderd/devtunnel/tunnel_test.go
+++ b/coderd/devtunnel/tunnel_test.go
@@ -2,11 +2,13 @@ package devtunnel_test
 
 import (
 	"context"
+	"io"
 	"net"
 	"net/http"
 	"testing"
 	"time"
 
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
 	"cdr.dev/slog/sloggers/slogtest"
@@ -47,17 +49,29 @@ func TestTunnel(t *testing.T) {
 	go server.Serve(tun.Listener)
 	defer tun.Listener.Close()
 
+	transport, _ := http.DefaultTransport.(*http.Transport)
+
+	httpClient := &http.Client{
+		Transport: transport,
+		Timeout:   10 * time.Second,
+	}
+
 	require.Eventually(t, func() bool {
 		req, err := http.NewRequestWithContext(ctx, "GET", tun.URL, nil)
 		require.NoError(t, err)
 
-		res, err := http.DefaultClient.Do(req)
+		res, err := httpClient.Do(req)
 		require.NoError(t, err)
 		defer res.Body.Close()
+		_, _ = io.Copy(io.Discard, res.Body)
+
 		return res.StatusCode == http.StatusOK
 	}, time.Minute, time.Second)
 
+	httpClient.CloseIdleConnections()
+	assert.NoError(t, server.Close())
 	cancelTun()
+
 	select {
 	case <-errCh:
 	case <-time.After(10 * time.Second):

From fa0328d25997d72db931998a380df0c5db7b9b3d Mon Sep 17 00:00:00 2001
From: Colin Adler <colin1adler@gmail.com>
Date: Fri, 10 Jun 2022 18:30:07 -0500
Subject: [PATCH 2/2] fixup! fix(devtunnel): close `http.Server` before
 wireguard interface

---
 coderd/devtunnel/tunnel_test.go | 5 +----
 1 file changed, 1 insertion(+), 4 deletions(-)

diff --git a/coderd/devtunnel/tunnel_test.go b/coderd/devtunnel/tunnel_test.go
index 9b549cabb1063..3ea8a63809a0c 100644
--- a/coderd/devtunnel/tunnel_test.go
+++ b/coderd/devtunnel/tunnel_test.go
@@ -49,11 +49,8 @@ func TestTunnel(t *testing.T) {
 	go server.Serve(tun.Listener)
 	defer tun.Listener.Close()
 
-	transport, _ := http.DefaultTransport.(*http.Transport)
-
 	httpClient := &http.Client{
-		Transport: transport,
-		Timeout:   10 * time.Second,
+		Timeout: 10 * time.Second,
 	}
 
 	require.Eventually(t, func() bool {