diff --git a/internal/deephash/deephash_test.go b/internal/deephash/deephash_test.go
index d99612adc..3d33bcd4a 100644
--- a/internal/deephash/deephash_test.go
+++ b/internal/deephash/deephash_test.go
@@ -51,14 +51,23 @@ func getVal() []interface{} {
 		map[dnsname.FQDN][]netaddr.IP{
 			dnsname.FQDN("a."): {netaddr.MustParseIP("1.2.3.4"), netaddr.MustParseIP("4.3.2.1")},
 			dnsname.FQDN("b."): {netaddr.MustParseIP("8.8.8.8"), netaddr.MustParseIP("9.9.9.9")},
+			dnsname.FQDN("c."): {netaddr.MustParseIP("6.6.6.6"), netaddr.MustParseIP("7.7.7.7")},
+			dnsname.FQDN("d."): {netaddr.MustParseIP("6.7.6.6"), netaddr.MustParseIP("7.7.7.8")},
+			dnsname.FQDN("e."): {netaddr.MustParseIP("6.8.6.6"), netaddr.MustParseIP("7.7.7.9")},
+			dnsname.FQDN("f."): {netaddr.MustParseIP("6.9.6.6"), netaddr.MustParseIP("7.7.7.0")},
 		},
 		map[dnsname.FQDN][]netaddr.IPPort{
 			dnsname.FQDN("a."): {netaddr.MustParseIPPort("1.2.3.4:11"), netaddr.MustParseIPPort("4.3.2.1:22")},
 			dnsname.FQDN("b."): {netaddr.MustParseIPPort("8.8.8.8:11"), netaddr.MustParseIPPort("9.9.9.9:22")},
+			dnsname.FQDN("c."): {netaddr.MustParseIPPort("8.8.8.8:12"), netaddr.MustParseIPPort("9.9.9.9:23")},
+			dnsname.FQDN("d."): {netaddr.MustParseIPPort("8.8.8.8:13"), netaddr.MustParseIPPort("9.9.9.9:24")},
+			dnsname.FQDN("e."): {netaddr.MustParseIPPort("8.8.8.8:14"), netaddr.MustParseIPPort("9.9.9.9:25")},
 		},
 		map[tailcfg.DiscoKey]bool{
 			{1: 1}: true,
 			{1: 2}: false,
+			{2: 3}: true,
+			{3: 4}: false,
 		},
 	}
 }
diff --git a/ipn/message.go b/ipn/message.go
index d8b7d1396..fb5638eca 100644
--- a/ipn/message.go
+++ b/ipn/message.go
@@ -104,7 +104,9 @@ func NewBackendServer(logf logger.Logf, b Backend, sendNotifyMsg func(Notify)) *
 		b:             b,
 		sendNotifyMsg: sendNotifyMsg,
 	}
-	if sendNotifyMsg != nil {
+	// b may be nil if the BackendServer is being created just to
+	// encapsulate and send an error message.
+	if sendNotifyMsg != nil && b != nil {
 		b.SetNotifyCallback(bs.send)
 	}
 	return bs
diff --git a/ipn/message_test.go b/ipn/message_test.go
index 79c4a76b6..194ac3b89 100644
--- a/ipn/message_test.go
+++ b/ipn/message_test.go
@@ -187,3 +187,17 @@ func TestClientServer(t *testing.T) {
 	})
 	flushUntil(Running)
 }
+
+func TestNilBackend(t *testing.T) {
+	var called *Notify
+	bs := NewBackendServer(t.Logf, nil, func(n Notify) {
+		called = &n
+	})
+	bs.SendErrorMessage("Danger, Will Robinson!")
+	if called == nil {
+		t.Errorf("expect callback to be called, wasn't")
+	}
+	if called.ErrMessage == nil || *called.ErrMessage != "Danger, Will Robinson!" {
+		t.Errorf("callback got wrong error: %v", called.ErrMessage)
+	}
+}