diff --git a/wgengine/magicsock/derp.go b/wgengine/magicsock/derp.go
index 9c60e4893..b5fc36bb8 100644
--- a/wgengine/magicsock/derp.go
+++ b/wgengine/magicsock/derp.go
@@ -91,7 +91,7 @@ func (c *Conn) fallbackDERPRegionForPeer(peer key.NodePublic) (regionID int) {
 type activeDerp struct {
 	c       *derphttp.Client
 	cancel  context.CancelFunc
-	writeCh chan<- derpWriteRequest
+	writeCh chan derpWriteRequest
 	// lastWrite is the time of the last request for its write
 	// channel (currently even if there was no write).
 	// It is always non-nil and initialized to a non-zero Time.
@@ -302,7 +302,7 @@ const derpWriteQueueDepth = 32
 //
 // It returns nil if the network is down, the Conn is closed, or the regionID is
 // not known.
-func (c *Conn) derpWriteChanForRegion(regionID int, peer key.NodePublic) chan<- derpWriteRequest {
+func (c *Conn) derpWriteChanForRegion(regionID int, peer key.NodePublic) chan derpWriteRequest {
 	if c.networkDown() {
 		return nil
 	}
diff --git a/wgengine/magicsock/magicsock.go b/wgengine/magicsock/magicsock.go
index a7f84e352..a11e8a1cd 100644
--- a/wgengine/magicsock/magicsock.go
+++ b/wgengine/magicsock/magicsock.go
@@ -1642,18 +1642,27 @@ func (c *Conn) sendAddr(addr netip.AddrPort, pubKey key.NodePublic, b []byte, is
 	// internal locks.
 	pkt := bytes.Clone(b)
 
-	select {
-	case <-c.donec:
-		metricSendDERPErrorClosed.Add(1)
-		return false, errConnClosed
-	case ch <- derpWriteRequest{addr, pubKey, pkt, isDisco}:
-		metricSendDERPQueued.Add(1)
-		return true, nil
-	default:
-		metricSendDERPErrorQueue.Add(1)
-		// Too many writes queued. Drop packet.
-		return false, errDropDerpPacket
+	wr := derpWriteRequest{addr, pubKey, pkt, isDisco}
+	for range 3 {
+		select {
+		case <-c.donec:
+			metricSendDERPErrorClosed.Add(1)
+			return false, errConnClosed
+		case ch <- wr:
+			metricSendDERPQueued.Add(1)
+			return true, nil
+		default:
+			select {
+			case <-ch:
+				metricSendDERPDropped.Add(1)
+			default:
+			}
+		}
 	}
+	// gave up after 3 write attempts
+	metricSendDERPErrorQueue.Add(1)
+	// Too many writes queued. Drop packet.
+	return false, errDropDerpPacket
 }
 
 type receiveBatch struct {
@@ -3937,6 +3946,7 @@ var (
 	metricSendDERPErrorChan   = clientmetric.NewCounter("magicsock_send_derp_error_chan")
 	metricSendDERPErrorClosed = clientmetric.NewCounter("magicsock_send_derp_error_closed")
 	metricSendDERPErrorQueue  = clientmetric.NewCounter("magicsock_send_derp_error_queue")
+	metricSendDERPDropped     = clientmetric.NewCounter("magicsock_send_derp_dropped")
 	metricSendUDP             = clientmetric.NewAggregateCounter("magicsock_send_udp")
 	metricSendUDPError        = clientmetric.NewCounter("magicsock_send_udp_error")
 	metricSendPeerRelay       = clientmetric.NewAggregateCounter("magicsock_send_peer_relay")