coder · mafredri · Feb 24, 2023 · Feb 21, 2023 · Feb 21, 2023 · Feb 21, 2023
diff --git a/coderd/coderd_test.go b/coderd/coderd_test.go
@@ -6,6 +6,7 @@ import (
 	"net/http"
 	"net/netip"
 	"strconv"
+	"sync"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -78,8 +79,14 @@ func TestDERP(t *testing.T) {
 		DERPMap:   derpMap,
 	})
 	require.NoError(t, err)
+
+	w2Ready := make(chan struct{}, 1)
+	w2ReadyOnce := sync.Once{}
 	w1.SetNodeCallback(func(node *tailnet.Node) {
 		w2.UpdateNodes([]*tailnet.Node{node})
+		w2ReadyOnce.Do(func() {
+			close(w2Ready)
+		})
 	})
 	w2.SetNodeCallback(func(node *tailnet.Node) {
 		w1.UpdateNodes([]*tailnet.Node{node})
@@ -98,6 +105,7 @@ func TestDERP(t *testing.T) {
 	}()
 
 	<-conn
+	<-w2Ready
 	nc, err := w2.DialContextTCP(context.Background(), netip.AddrPortFrom(w1IP, 35565))
 	require.NoError(t, err)
 	_ = nc.Close()

diff --git a/coderd/workspaceagents_test.go b/coderd/workspaceagents_test.go
@@ -469,6 +469,8 @@ func TestWorkspaceAgentListeningPorts(t *testing.T) {
 	t.Parallel()
 
 	setup := func(t *testing.T, apps []*proto.App) (*codersdk.Client, uint16, uuid.UUID) {
+		t.Helper()
+
 		client := coderdtest.New(t, &coderdtest.Options{
 			IncludeProvisionerDaemon: true,
 		})

diff --git a/coderd/wsconncache/wsconncache_test.go b/coderd/wsconncache/wsconncache_test.go
@@ -29,6 +29,7 @@ import (
 	"github.com/coder/coder/codersdk/agentsdk"
 	"github.com/coder/coder/tailnet"
 	"github.com/coder/coder/tailnet/tailnettest"
+	"github.com/coder/coder/testutil"
 )
 
 func TestMain(m *testing.M) {
@@ -131,6 +132,14 @@ func TestCache(t *testing.T) {
 					return
 				}
 				defer release()
+
+				ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitMedium)
+				defer cancel()
+				if !conn.AwaitReachable(ctx) {
+					t.Error("agent not reachable")
+					return
+				}
+
 				transport := conn.HTTPTransport()
 				defer transport.CloseIdleConnections()
 				proxy.Transport = transport
@@ -146,6 +155,8 @@ func TestCache(t *testing.T) {
 }
 
 func setupAgent(t *testing.T, metadata agentsdk.Metadata, ptyTimeout time.Duration) *codersdk.WorkspaceAgentConn {
+	t.Helper()
+
 	metadata.DERPMap = tailnettest.RunDERPAndSTUN(t)
 
 	coordinator := tailnet.NewCoordinator()

diff --git a/codersdk/workspaceagentconn.go b/codersdk/workspaceagentconn.go
@@ -176,7 +176,9 @@ type ReconnectingPTYRequest struct {
 func (c *WorkspaceAgentConn) ReconnectingPTY(ctx context.Context, id uuid.UUID, height, width uint16, command string) (net.Conn, error) {
 	ctx, span := tracing.StartSpan(ctx)
 	defer span.End()
-
+	if !c.AwaitReachable(ctx) {
+		return nil, xerrors.Errorf("workspace agent not reachable in time: %v", ctx.Err())
+	}
 	conn, err := c.DialContextTCP(ctx, netip.AddrPortFrom(WorkspaceAgentIP, WorkspaceAgentReconnectingPTYPort))
 	if err != nil {
 		return nil, err
@@ -207,6 +209,9 @@ func (c *WorkspaceAgentConn) ReconnectingPTY(ctx context.Context, id uuid.UUID,
 func (c *WorkspaceAgentConn) SSH(ctx context.Context) (net.Conn, error) {
 	ctx, span := tracing.StartSpan(ctx)
 	defer span.End()
+	if !c.AwaitReachable(ctx) {
+		return nil, xerrors.Errorf("workspace agent not reachable in time: %v", ctx.Err())
+	}
 	return c.DialContextTCP(ctx, netip.AddrPortFrom(WorkspaceAgentIP, WorkspaceAgentSSHPort))
 }
 
@@ -235,6 +240,9 @@ func (c *WorkspaceAgentConn) SSHClient(ctx context.Context) (*ssh.Client, error)
 func (c *WorkspaceAgentConn) Speedtest(ctx context.Context, direction speedtest.Direction, duration time.Duration) ([]speedtest.Result, error) {
 	ctx, span := tracing.StartSpan(ctx)
 	defer span.End()
+	if !c.AwaitReachable(ctx) {
+		return nil, xerrors.Errorf("workspace agent not reachable in time: %v", ctx.Err())
+	}
 	speedConn, err := c.DialContextTCP(ctx, netip.AddrPortFrom(WorkspaceAgentIP, WorkspaceAgentSpeedtestPort))
 	if err != nil {
 		return nil, xerrors.Errorf("dial speedtest: %w", err)
@@ -257,6 +265,9 @@ func (c *WorkspaceAgentConn) DialContext(ctx context.Context, network string, ad
 	_, rawPort, _ := net.SplitHostPort(addr)
 	port, _ := strconv.ParseUint(rawPort, 10, 16)
 	ipp := netip.AddrPortFrom(WorkspaceAgentIP, uint16(port))
+	if !c.AwaitReachable(ctx) {
+		return nil, xerrors.Errorf("workspace agent not reachable in time: %v", ctx.Err())
+	}
 	if network == "udp" {
 		return c.Conn.DialContextUDP(ctx, ipp)
 	}
@@ -317,7 +328,7 @@ func (c *WorkspaceAgentConn) apiClient() *http.Client {
 			// Disable keep alives as we're usually only making a single
 			// request, and this triggers goleak in tests
 			DisableKeepAlives: true,
-			DialContext: func(_ context.Context, network, addr string) (net.Conn, error) {
+			DialContext: func(ctx context.Context, network, addr string) (net.Conn, error) {
 				if network != "tcp" {
 					return nil, xerrors.Errorf("network must be tcp")
 				}
@@ -331,7 +342,11 @@ func (c *WorkspaceAgentConn) apiClient() *http.Client {
 					return nil, xerrors.Errorf("request %q does not appear to be for http api", addr)
 				}
 
-				conn, err := c.DialContextTCP(context.Background(), netip.AddrPortFrom(WorkspaceAgentIP, WorkspaceAgentHTTPAPIServerPort))
+				if !c.AwaitReachable(ctx) {
+					return nil, xerrors.Errorf("workspace agent not reachable in time: %v", ctx.Err())
+				}
+
+				conn, err := c.DialContextTCP(ctx, netip.AddrPortFrom(WorkspaceAgentIP, WorkspaceAgentHTTPAPIServerPort))
 				if err != nil {
 					return nil, xerrors.Errorf("dial http api: %w", err)
 				}

diff --git a/codersdk/workspaceagents.go b/codersdk/workspaceagents.go
@@ -199,13 +199,19 @@ func (c *Client) DialWorkspaceAgent(ctx context.Context, agentID uuid.UUID, opti
 		return nil, err
 	}
 
-	return &WorkspaceAgentConn{
+	agentConn := &WorkspaceAgentConn{
 		Conn: conn,
 		CloseFunc: func() {
 			cancelFunc()
 			<-closed
 		},
-	}, nil
+	}
+	if !agentConn.AwaitReachable(ctx) {
+		_ = agentConn.Close()
+		return nil, xerrors.Errorf("timed out waiting for agent to become reachable: %w", ctx.Err())
+	}
+
+	return agentConn, nil
 }
 
 // WorkspaceAgent returns an agent by ID.

diff --git a/tailnet/conn.go b/tailnet/conn.go
@@ -60,7 +60,7 @@ type Options struct {
 }
 
 // NewConn constructs a new Wireguard server that will accept connections from the addresses provided.
-func NewConn(options *Options) (*Conn, error) {
+func NewConn(options *Options) (conn *Conn, err error) {
 	if options == nil {
 		options = &Options{}
 	}
@@ -123,6 +123,11 @@ func NewConn(options *Options) (*Conn, error) {
 	if err != nil {
 		return nil, xerrors.Errorf("create wireguard link monitor: %w", err)
 	}
+	defer func() {
+		if err != nil {
+			wireguardMonitor.Close()
+		}
+	}()
 
 	dialer := &tsdial.Dialer{
 		Logf: Logger(options.Logger),
@@ -134,6 +139,11 @@ func NewConn(options *Options) (*Conn, error) {
 	if err != nil {
 		return nil, xerrors.Errorf("create wgengine: %w", err)
 	}
+	defer func() {
+		if err != nil {
+			wireguardEngine.Close()
+		}
+	}()
 	dialer.UseNetstackForIP = func(ip netip.Addr) bool {
 		_, ok := wireguardEngine.PeerForIP(ip)
 		return ok
@@ -166,10 +176,6 @@ func NewConn(options *Options) (*Conn, error) {
 		return netStack.DialContextTCP(ctx, dst)
 	}
 	netStack.ProcessLocalIPs = true
-	err = netStack.Start(nil)
-	if err != nil {
-		return nil, xerrors.Errorf("start netstack: %w", err)
-	}
 	wireguardEngine = wgengine.NewWatchdog(wireguardEngine)
 	wireguardEngine.SetDERPMap(options.DERPMap)
 	netMapCopy := *netMap
@@ -203,6 +209,11 @@ func NewConn(options *Options) (*Conn, error) {
 		},
 		wireguardEngine: wireguardEngine,
 	}
+	defer func() {
+		if err != nil {
+			_ = server.Close()
+		}
+	}()
 	wireguardEngine.SetStatusCallback(func(s *wgengine.Status, err error) {
 		server.logger.Debug(context.Background(), "wireguard status", slog.F("status", s), slog.F("err", err))
 		if err != nil {
@@ -236,6 +247,12 @@ func NewConn(options *Options) (*Conn, error) {
 		server.sendNode()
 	})
 	netStack.ForwardTCPIn = server.forwardTCP
+
+	err = netStack.Start(nil)
+	if err != nil {
+		return nil, xerrors.Errorf("start netstack: %w", err)
+	}
+
 	return server, nil
 }
 
@@ -519,22 +536,35 @@ func (c *Conn) Close() error {
 	default:
 	}
 	close(c.closed)
-	for _, l := range c.listeners {
-		_ = l.closeNoLock()
-	}
 	c.mutex.Unlock()
-	c.dialCancel()
-	_ = c.dialer.Close()
-	_ = c.magicConn.Close()
+
+	var wg sync.WaitGroup
+	defer wg.Wait()
+
+	if c.trafficStats != nil {
+		wg.Add(1)
+		go func() {
+			defer wg.Done()
+			ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+			defer cancel()
+			_ = c.trafficStats.Shutdown(ctx)
+		}()
+	}
+
 	_ = c.netStack.Close()
+	c.dialCancel()
 	_ = c.wireguardMonitor.Close()
-	_ = c.tunDevice.Close()
+	_ = c.dialer.Close()
+	// Stops internals, e.g. tunDevice, magicConn and dnsManager.
 	c.wireguardEngine.Close()
-	if c.trafficStats != nil {
-		ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
-		defer cancel()
-		_ = c.trafficStats.Shutdown(ctx)
+
+	c.mutex.Lock()
+	for _, l := range c.listeners {
+		_ = l.closeNoLock()
 	}
+	c.listeners = nil
+	c.mutex.Unlock()
+
 	return nil
 }
 
@@ -714,16 +744,25 @@ func (c *Conn) forwardTCPToLocal(conn net.Conn, port uint16) {
 func (c *Conn) SetConnStatsCallback(maxPeriod time.Duration, maxConns int, dump func(start, end time.Time, virtual, physical map[netlogtype.Connection]netlogtype.Counts)) {
 	connStats := connstats.NewStatistics(maxPeriod, maxConns, dump)
 
+	shutdown := func(s *connstats.Statistics) {
+		ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+		defer cancel()
+		_ = s.Shutdown(ctx)
+	}
+
 	c.mutex.Lock()
+	if c.isClosed() {
+		c.mutex.Unlock()
+		shutdown(connStats)
+		return
+	}
 	old := c.trafficStats
 	c.trafficStats = connStats
 	c.mutex.Unlock()
 
 	// Make sure to shutdown the old callback.
 	if old != nil {
-		ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
-		defer cancel()
-		_ = old.Shutdown(ctx)
+		shutdown(old)
 	}
 
 	c.tunDevice.SetStatistics(connStats)
@@ -776,6 +815,7 @@ func (a addr) String() string  { return a.ln.addr }
 // Logger converts the Tailscale logging function to use slog.
 func Logger(logger slog.Logger) tslogger.Logf {
 	return tslogger.Logf(func(format string, args ...any) {
+		slog.Helper()
 		logger.Debug(context.Background(), fmt.Sprintf(format, args...))
 	})
 }