diff --git a/derp/derphttp/derphttp_client.go b/derp/derphttp/derphttp_client.go
index 500162932..f2e64368c 100644
--- a/derp/derphttp/derphttp_client.go
+++ b/derp/derphttp/derphttp_client.go
@@ -13,6 +13,7 @@ package derphttp
 import (
 	"bufio"
 	"context"
+	"crypto/rand"
 	"crypto/tls"
 	"crypto/x509"
 	"errors"
@@ -72,6 +73,7 @@ type Client struct {
 	client       *derp.Client
 	connGen      int // incremented once per new connection; valid values are >0
 	serverPubKey key.NodePublic
+	pingOut      map[derp.PingMessage]chan<- bool // chan to send to on pong
 }
 
 // NewRegionClient returns a new DERP-over-HTTP client. It connects lazily.
@@ -698,7 +700,67 @@ func (c *Client) Send(dstKey key.NodePublic, b []byte) error {
 	return err
 }
 
-// SendPing sends a ping message, without any implicit connect or reconnect.
+func (c *Client) registerPing(m derp.PingMessage, ch chan<- bool) {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	if c.pingOut == nil {
+		c.pingOut = map[derp.PingMessage]chan<- bool{}
+	}
+	c.pingOut[m] = ch
+}
+
+func (c *Client) unregisterPing(m derp.PingMessage) {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	delete(c.pingOut, m)
+}
+
+func (c *Client) handledPong(m derp.PongMessage) bool {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	k := derp.PingMessage(m)
+	if ch, ok := c.pingOut[k]; ok {
+		ch <- true
+		delete(c.pingOut, k)
+		return true
+	}
+	return false
+}
+
+// Ping sends a ping to the peer and waits for it either to be
+// acknowledged (in which case Ping returns nil) or waits for ctx to
+// be over and returns an error. It will wait at most 5 seconds
+// before returning an error.
+//
+// Another goroutine must be in a loop calling Recv or
+// RecvDetail or ping responses won't be handled.
+func (c *Client) Ping(ctx context.Context) error {
+	maxDL := time.Now().Add(5 * time.Second)
+	if dl, ok := ctx.Deadline(); !ok || dl.After(maxDL) {
+		var cancel context.CancelFunc
+		ctx, cancel = context.WithDeadline(ctx, maxDL)
+		defer cancel()
+	}
+	var data derp.PingMessage
+	rand.Read(data[:])
+	gotPing := make(chan bool, 1)
+	c.registerPing(data, gotPing)
+	defer c.unregisterPing(data)
+	if err := c.SendPing(data); err != nil {
+		return err
+	}
+	select {
+	case <-gotPing:
+		return nil
+	case <-ctx.Done():
+		return ctx.Err()
+	}
+}
+
+// SendPing writes a ping message, without any implicit connect or
+// reconnect. This is a lower-level interface that writes a frame
+// without any implicit handling of the response pong, if any. For a
+// higher-level interface, use Ping.
 func (c *Client) SendPing(data [8]byte) error {
 	c.mu.Lock()
 	closed, client := c.closed, c.client
@@ -819,14 +881,22 @@ func (c *Client) RecvDetail() (m derp.ReceivedMessage, connGen int, err error) {
 	if err != nil {
 		return nil, 0, err
 	}
-	m, err = client.Recv()
-	if err != nil {
-		c.closeForReconnect(client)
-		if c.isClosed() {
-			err = ErrClientClosed
+	for {
+		m, err = client.Recv()
+		switch m := m.(type) {
+		case derp.PongMessage:
+			if c.handledPong(m) {
+				continue
+			}
+		}
+		if err != nil {
+			c.closeForReconnect(client)
+			if c.isClosed() {
+				err = ErrClientClosed
+			}
 		}
+		return m, connGen, err
 	}
-	return m, connGen, err
 }
 
 func (c *Client) isClosed() bool {
diff --git a/derp/derphttp/derphttp_test.go b/derp/derphttp/derphttp_test.go
index 40cddc4da..bc6c008b2 100644
--- a/derp/derphttp/derphttp_test.go
+++ b/derp/derphttp/derphttp_test.go
@@ -154,3 +154,55 @@ func waitConnect(t testing.TB, c *Client) {
 		t.Fatalf("client first Recv was unexpected type %T", v)
 	}
 }
+
+func TestPing(t *testing.T) {
+	serverPrivateKey := key.NewNode()
+	s := derp.NewServer(serverPrivateKey, t.Logf)
+	defer s.Close()
+
+	httpsrv := &http.Server{
+		TLSNextProto: make(map[string]func(*http.Server, *tls.Conn, http.Handler)),
+		Handler:      Handler(s),
+	}
+
+	ln, err := net.Listen("tcp4", "localhost:0")
+	if err != nil {
+		t.Fatal(err)
+	}
+	serverURL := "http://" + ln.Addr().String()
+	t.Logf("server URL: %s", serverURL)
+
+	go func() {
+		if err := httpsrv.Serve(ln); err != nil {
+			if err == http.ErrServerClosed {
+				return
+			}
+			panic(err)
+		}
+	}()
+
+	c, err := NewClient(key.NewNode(), serverURL, t.Logf)
+	if err != nil {
+		t.Fatalf("NewClient: %v", err)
+	}
+	defer c.Close()
+	if err := c.Connect(context.Background()); err != nil {
+		t.Fatalf("client Connect: %v", err)
+	}
+
+	errc := make(chan error, 1)
+	go func() {
+		for {
+			m, err := c.Recv()
+			if err != nil {
+				errc <- err
+				return
+			}
+			t.Logf("Recv: %T", m)
+		}
+	}()
+	err = c.Ping(context.Background())
+	if err != nil {
+		t.Fatalf("Ping: %v", err)
+	}
+}