diff --git a/derp/derp_server.go b/derp/derp_server.go
index 70957a138..42855e0b3 100644
--- a/derp/derp_server.go
+++ b/derp/derp_server.go
@@ -36,6 +36,7 @@ import (
 	"go4.org/mem"
 	"golang.org/x/crypto/nacl/box"
 	"golang.org/x/sync/errgroup"
+	"golang.org/x/time/rate"
 	"inet.af/netaddr"
 	"tailscale.com/client/tailscale"
 	"tailscale.com/disco"
@@ -118,6 +119,8 @@ type Server struct {
 	curClients                   expvar.Int
 	curHomeClients               expvar.Int // ones with preferred
 	clientsReplaced              expvar.Int
+	clientsReplaceLimited        expvar.Int
+	clientsReplaceSleeping       expvar.Int
 	unknownFrames                expvar.Int
 	homeMovesIn                  expvar.Int // established clients announce home server moves in
 	homeMovesOut                 expvar.Int // established clients announce home server moves out
@@ -346,14 +349,28 @@ func (s *Server) initMetacert() {
 func (s *Server) MetaCert() []byte { return s.metaCert }
 
 // registerClient notes that client c is now authenticated and ready for packets.
-// If c's public key was already connected with a different connection, the prior one is closed.
-func (s *Server) registerClient(c *sclient) {
+//
+// If c's public key was already connected with a different
+// connection, the prior one is closed, unless it's fighting rapidly
+// with another client with the same key, in which case the returned
+// ok is false, and the caller should wait the provided duration
+// before trying again.
+func (s *Server) registerClient(c *sclient) (ok bool, d time.Duration) {
 	s.mu.Lock()
 	defer s.mu.Unlock()
 	old := s.clients[c.key]
 	if old == nil {
 		c.logf("adding connection")
 	} else {
+		// Take over the old rate limiter, discarding the one
+		// our caller just made.
+		c.replaceLimiter = old.replaceLimiter
+		if rr := c.replaceLimiter.ReserveN(timeNow(), 1); rr.OK() {
+			if d := rr.DelayFrom(timeNow()); d > 0 {
+				s.clientsReplaceLimited.Add(1)
+				return false, d
+			}
+		}
 		s.clientsReplaced.Add(1)
 		c.logf("adding connection, replacing %s", old.remoteAddr)
 		go old.nc.Close()
@@ -365,6 +382,7 @@ func (s *Server) registerClient(c *sclient) {
 	s.keyOfAddr[c.remoteIPPort] = c.key
 	s.curClients.Add(1)
 	s.broadcastPeerStateChangeLocked(c.key, true)
+	return true, 0
 }
 
 // broadcastPeerStateChangeLocked enqueues a message to all watchers
@@ -490,7 +508,14 @@ func (s *Server) accept(nc Conn, brw *bufio.ReadWriter, remoteAddr string, connN
 		discoSendQueue: make(chan pkt, perClientSendQueueDepth),
 		peerGone:       make(chan key.Public),
 		canMesh:        clientInfo.MeshKey != "" && clientInfo.MeshKey == s.meshKey,
+
+		// Allow kicking out previous connections once a
+		// minute, with a very high burst of 100. Once a
+		// minute is less than the client's 2 minute
+		// inactivity timeout.
+		replaceLimiter: rate.NewLimiter(rate.Every(time.Minute), 100),
 	}
+
 	if c.canMesh {
 		c.meshUpdate = make(chan struct{})
 	}
@@ -498,7 +523,15 @@ func (s *Server) accept(nc Conn, brw *bufio.ReadWriter, remoteAddr string, connN
 		c.info = *clientInfo
 	}
 
-	s.registerClient(c)
+	for {
+		ok, d := s.registerClient(c)
+		if ok {
+			break
+		}
+		s.clientsReplaceSleeping.Add(1)
+		timeSleep(d)
+		s.clientsReplaceSleeping.Add(-1)
+	}
 	defer s.unregisterClient(c)
 
 	err = s.sendServerInfo(bw, clientKey)
@@ -509,6 +542,12 @@ func (s *Server) accept(nc Conn, brw *bufio.ReadWriter, remoteAddr string, connN
 	return c.run(ctx)
 }
 
+// for testing
+var (
+	timeSleep = time.Sleep
+	timeNow   = time.Now
+)
+
 // run serves the client until there's an error.
 // If the client hangs up or the server is closed, run returns nil, otherwise run returns an error.
 func (c *sclient) run(ctx context.Context) error {
@@ -952,6 +991,11 @@ type sclient struct {
 	meshUpdate     chan struct{}   // write request to write peerStateChange
 	canMesh        bool            // clientInfo had correct mesh token for inter-region routing
 
+	// replaceLimiter controls how quickly two connections with
+	// the same client key can kick each other off the server by
+	// taking over ownership of a key.
+	replaceLimiter *rate.Limiter
+
 	// Owned by run, not thread-safe.
 	br          *bufio.Reader
 	connectedAt time.Time
@@ -1351,6 +1395,8 @@ func (s *Server) ExpVar() expvar.Var {
 	m.Set("gauge_clients_remote", expvar.Func(func() interface{} { return len(s.clientsMesh) - len(s.clients) }))
 	m.Set("accepts", &s.accepts)
 	m.Set("clients_replaced", &s.clientsReplaced)
+	m.Set("clients_replace_limited", &s.clientsReplaceLimited)
+	m.Set("gauge_clients_replace_sleeping", &s.clientsReplaceSleeping)
 	m.Set("bytes_received", &s.bytesRecv)
 	m.Set("bytes_sent", &s.bytesSent)
 	m.Set("packets_dropped", &s.packetsDropped)
diff --git a/derp/derp_test.go b/derp/derp_test.go
index a37dd0390..d8dfa714b 100644
--- a/derp/derp_test.go
+++ b/derp/derp_test.go
@@ -23,6 +23,7 @@ import (
 	"testing"
 	"time"
 
+	"golang.org/x/time/rate"
 	"tailscale.com/net/nettest"
 	"tailscale.com/types/key"
 	"tailscale.com/types/logger"
@@ -849,6 +850,136 @@ func TestClientSendPong(t *testing.T) {
 
 }
 
+func TestServerReplaceClients(t *testing.T) {
+	defer func() {
+		timeSleep = time.Sleep
+		timeNow = time.Now
+	}()
+
+	var (
+		mu     sync.Mutex
+		now    = time.Unix(123, 0)
+		sleeps int
+		slept  time.Duration
+	)
+	timeSleep = func(d time.Duration) {
+		mu.Lock()
+		defer mu.Unlock()
+		sleeps++
+		slept += d
+		now = now.Add(d)
+	}
+	timeNow = func() time.Time {
+		mu.Lock()
+		defer mu.Unlock()
+		return now
+	}
+
+	serverPrivateKey := newPrivateKey(t)
+	var logger logger.Logf = logger.Discard
+	const debug = false
+	if debug {
+		logger = t.Logf
+	}
+
+	s := NewServer(serverPrivateKey, logger)
+	defer s.Close()
+
+	priv := newPrivateKey(t)
+
+	ln, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer ln.Close()
+
+	connNum := 0
+	connect := func() *Client {
+		connNum++
+		cout, err := net.Dial("tcp", ln.Addr().String())
+		if err != nil {
+			t.Fatal(err)
+		}
+
+		cin, err := ln.Accept()
+		if err != nil {
+			t.Fatal(err)
+		}
+
+		brwServer := bufio.NewReadWriter(bufio.NewReader(cin), bufio.NewWriter(cin))
+		go s.Accept(cin, brwServer, fmt.Sprintf("test-client-%d", connNum))
+
+		brw := bufio.NewReadWriter(bufio.NewReader(cout), bufio.NewWriter(cout))
+		c, err := NewClient(priv, cout, brw, logger)
+		if err != nil {
+			t.Fatalf("client %d: %v", connNum, err)
+		}
+		return c
+	}
+
+	wantVar := func(v *expvar.Int, want int64) {
+		t.Helper()
+		if got := v.Value(); got != want {
+			t.Errorf("got %d; want %d", got, want)
+		}
+	}
+
+	wantClosed := func(c *Client) {
+		t.Helper()
+		for {
+			m, err := c.Recv()
+			if err != nil {
+				t.Logf("got expected error: %v", err)
+				return
+			}
+			switch m.(type) {
+			case ServerInfoMessage:
+				continue
+			default:
+				t.Fatalf("client got %T; wanted an error", m)
+			}
+		}
+	}
+
+	c1 := connect()
+	waitConnect(t, c1)
+	c2 := connect()
+	waitConnect(t, c2)
+	wantVar(&s.clientsReplaced, 1)
+	wantClosed(c1)
+
+	for i := 0; i < 100+5; i++ {
+		c := connect()
+		defer c.nc.Close()
+		if s.clientsReplaceLimited.Value() == 0 && i < 90 {
+			continue
+		}
+		t.Logf("for %d: replaced=%d, limited=%d, sleeping=%d", i,
+			s.clientsReplaced.Value(),
+			s.clientsReplaceLimited.Value(),
+			s.clientsReplaceSleeping.Value(),
+		)
+	}
+
+	mu.Lock()
+	defer mu.Unlock()
+	if sleeps == 0 {
+		t.Errorf("no sleeps")
+	}
+	if slept == 0 {
+		t.Errorf("total sleep duration was 0")
+	}
+}
+
+func TestLimiter(t *testing.T) {
+	rl := rate.NewLimiter(rate.Every(time.Minute), 100)
+	for i := 0; i < 200; i++ {
+		r := rl.Reserve()
+		d := r.Delay()
+		t.Logf("i=%d, allow=%v, d=%v", i, r.OK(), d)
+	}
+}
+
 func BenchmarkSendRecv(b *testing.B) {
 	for _, size := range []int{10, 100, 1000, 10000} {
 		b.Run(fmt.Sprintf("msgsize=%d", size), func(b *testing.B) { benchmarkSendRecvSize(b, size) })