diff --git a/wgengine/magicsock/magicsock_test.go b/wgengine/magicsock/magicsock_test.go
index 4890ea70a..26c157d16 100644
--- a/wgengine/magicsock/magicsock_test.go
+++ b/wgengine/magicsock/magicsock_test.go
@@ -11,6 +11,7 @@ import (
 	"crypto/tls"
 	"encoding/binary"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"io/ioutil"
 	"net"
@@ -927,30 +928,45 @@ func testTwoDevicePing(t *testing.T, d *devices) {
 	// Retries take 5s each. Add 1s for some processing time.
 	pingTimeout := 5*time.Second*time.Duration(allowedRetries) + time.Second
 
+	// sendWithTimeout sends msg using send, checking that it is received unchanged from in.
+	// It resends once per second until the send succeeds, or pingTimeout time has elapsed.
+	sendWithTimeout := func(msg []byte, in chan []byte, send func()) error {
+		start := time.Now()
+		for time.Since(start) < pingTimeout {
+			send()
+			select {
+			case recv := <-in:
+				if !bytes.Equal(msg, recv) {
+					return errors.New("ping did not transit correctly")
+				}
+				return nil
+			case <-time.After(time.Second):
+				// try again
+			}
+		}
+		return errors.New("ping timed out")
+	}
+
 	ping1 := func(t *testing.T) {
 		msg2to1 := tuntest.Ping(net.ParseIP("1.0.0.1"), net.ParseIP("1.0.0.2"))
-		m2.tun.Outbound <- msg2to1
-		t.Log("ping1 sent")
-		select {
-		case msgRecv := <-m1.tun.Inbound:
-			if !bytes.Equal(msg2to1, msgRecv) {
-				t.Error("ping did not transit correctly")
-			}
-		case <-time.After(pingTimeout):
-			t.Error("ping did not transit")
+		send := func() {
+			m2.tun.Outbound <- msg2to1
+			t.Log("ping1 sent")
+		}
+		in := m1.tun.Inbound
+		if err := sendWithTimeout(msg2to1, in, send); err != nil {
+			t.Error(err)
 		}
 	}
 	ping2 := func(t *testing.T) {
 		msg1to2 := tuntest.Ping(net.ParseIP("1.0.0.2"), net.ParseIP("1.0.0.1"))
-		m1.tun.Outbound <- msg1to2
-		t.Log("ping2 sent")
-		select {
-		case msgRecv := <-m2.tun.Inbound:
-			if !bytes.Equal(msg1to2, msgRecv) {
-				t.Error("return ping did not transit correctly")
-			}
-		case <-time.After(pingTimeout):
-			t.Error("return ping did not transit")
+		send := func() {
+			m1.tun.Outbound <- msg1to2
+			t.Log("ping2 sent")
+		}
+		in := m2.tun.Inbound
+		if err := sendWithTimeout(msg1to2, in, send); err != nil {
+			t.Error(err)
 		}
 	}
 
@@ -971,17 +987,15 @@ func testTwoDevicePing(t *testing.T, d *devices) {
 		setT(t)
 		defer setT(outerT)
 		msg1to2 := tuntest.Ping(net.ParseIP("1.0.0.2"), net.ParseIP("1.0.0.1"))
-		if err := m1.tsTun.InjectOutbound(msg1to2); err != nil {
-			t.Fatal(err)
-		}
-		t.Log("SendPacket sent")
-		select {
-		case msgRecv := <-m2.tun.Inbound:
-			if !bytes.Equal(msg1to2, msgRecv) {
-				t.Error("return ping did not transit correctly")
+		send := func() {
+			if err := m1.tsTun.InjectOutbound(msg1to2); err != nil {
+				t.Fatal(err)
 			}
-		case <-time.After(pingTimeout):
-			t.Error("return ping did not transit")
+			t.Log("SendPacket sent")
+		}
+		in := m2.tun.Inbound
+		if err := sendWithTimeout(msg1to2, in, send); err != nil {
+			t.Error(err)
 		}
 	})