diff --git a/connection.go b/connection.go
index b1e9aaee3..0b009fbd6 100644
--- a/connection.go
+++ b/connection.go
@@ -155,6 +155,8 @@ type connection struct {
 	packer        packer
 	mtuDiscoverer mtuDiscoverer // initialized when the handshake completes
 
+	maxPayloadSizeEstimate atomic.Uint32
+
 	initialStream       cryptoStream
 	handshakeStream     cryptoStream
 	oneRTTStream        cryptoStream // only set for the server
@@ -274,9 +276,10 @@ var newConnection = func(
 	)
 	s.ctx, s.ctxCancel = context.WithCancelCause(context.WithValue(context.Background(), ConnectionTracingKey, tracingID))
 	s.preSetup()
+	initialPacketSize := getMaxPacketSize(s.conn.RemoteAddr())
 	s.sentPacketHandler, s.receivedPacketHandler = ackhandler.NewAckHandler(
 		0,
-		getMaxPacketSize(s.conn.RemoteAddr()),
+		initialPacketSize,
 		s.rttStats,
 		clientAddressValidated,
 		s.conn.capabilities().ECN,
@@ -284,7 +287,8 @@ var newConnection = func(
 		s.tracer,
 		s.logger,
 	)
-	s.mtuDiscoverer = newMTUDiscoverer(s.rttStats, getMaxPacketSize(s.conn.RemoteAddr()), s.sentPacketHandler.SetMaxDatagramSize)
+	s.mtuDiscoverer = newMTUDiscoverer(s.rttStats, initialPacketSize, s.onMTUIncreased)
+	s.maxPayloadSizeEstimate.Store(uint32(estimateMaxPayloadSize(initialPacketSize)))
 	params := &wire.TransportParameters{
 		InitialMaxStreamDataBidiLocal:   protocol.ByteCount(s.config.InitialStreamReceiveWindow),
 		InitialMaxStreamDataBidiRemote:  protocol.ByteCount(s.config.InitialStreamReceiveWindow),
@@ -383,9 +387,10 @@ var newClientConnection = func(
 	)
 	s.ctx, s.ctxCancel = context.WithCancelCause(context.WithValue(context.Background(), ConnectionTracingKey, tracingID))
 	s.preSetup()
+	initialPacketSize := getMaxPacketSize(s.conn.RemoteAddr())
 	s.sentPacketHandler, s.receivedPacketHandler = ackhandler.NewAckHandler(
 		initialPacketNumber,
-		getMaxPacketSize(s.conn.RemoteAddr()),
+		initialPacketSize,
 		s.rttStats,
 		false, // has no effect
 		s.conn.capabilities().ECN,
@@ -393,7 +398,8 @@ var newClientConnection = func(
 		s.tracer,
 		s.logger,
 	)
-	s.mtuDiscoverer = newMTUDiscoverer(s.rttStats, getMaxPacketSize(s.conn.RemoteAddr()), s.sentPacketHandler.SetMaxDatagramSize)
+	s.mtuDiscoverer = newMTUDiscoverer(s.rttStats, initialPacketSize, s.onMTUIncreased)
+	s.maxPayloadSizeEstimate.Store(uint32(estimateMaxPayloadSize(initialPacketSize)))
 	oneRTTStream := newCryptoStream()
 	params := &wire.TransportParameters{
 		InitialMaxStreamDataBidiRemote: protocol.ByteCount(s.config.InitialStreamReceiveWindow),
@@ -2352,13 +2358,23 @@ func (s *connection) onStreamCompleted(id protocol.StreamID) {
 	}
 }
 
+func (s *connection) onMTUIncreased(mtu protocol.ByteCount) {
+	s.maxPayloadSizeEstimate.Store(uint32(estimateMaxPayloadSize(mtu)))
+	s.sentPacketHandler.SetMaxDatagramSize(mtu)
+}
+
 func (s *connection) SendDatagram(p []byte) error {
 	if !s.supportsDatagrams() {
 		return errors.New("datagram support disabled")
 	}
 
 	f := &wire.DatagramFrame{DataLenPresent: true}
-	maxDataLen := f.MaxDataLen(s.peerParams.MaxDatagramFrameSize, s.version)
+	// The payload size estimate is conservative.
+	// Under many circumstances we could send a few more bytes.
+	maxDataLen := min(
+		f.MaxDataLen(s.peerParams.MaxDatagramFrameSize, s.version),
+		protocol.ByteCount(s.maxPayloadSizeEstimate.Load()),
+	)
 	if protocol.ByteCount(len(p)) > maxDataLen {
 		return &DatagramTooLargeError{MaxDatagramPayloadSize: int64(maxDataLen)}
 	}
@@ -2391,3 +2407,10 @@ func (s *connection) NextConnection() Connection {
 	s.streamsMap.UseResetMaps()
 	return s
 }
+
+// estimateMaxPayloadSize estimates the maximum payload size for short header packets.
+// It is not very sophisticated: it just subtracts the size of header (assuming the maximum
+// connection ID length), and the size of the encryption tag.
+func estimateMaxPayloadSize(mtu protocol.ByteCount) protocol.ByteCount {
+	return mtu - 1 /* type byte */ - 20 /* maximum connection ID length */ - 16 /* tag size */
+}
diff --git a/integrationtests/self/dplpmtud_test.go b/integrationtests/self/dplpmtud_test.go
index 4b5aae08d..402726322 100644
--- a/integrationtests/self/dplpmtud_test.go
+++ b/integrationtests/self/dplpmtud_test.go
@@ -17,10 +17,14 @@ import (
 
 var _ = Describe("DPLPMTUD", func() {
 	It("discovers the MTU", func() {
-		const rtt = 100 * time.Millisecond
+		rtt := scaleDuration(10 * time.Millisecond)
 		const mtu = 1400
 
-		ln, err := quic.ListenAddr("localhost:0", getTLSConfig(), getQuicConfig(&quic.Config{DisablePathMTUDiscovery: true}))
+		ln, err := quic.ListenAddr(
+			"localhost:0",
+			getTLSConfig(),
+			getQuicConfig(&quic.Config{DisablePathMTUDiscovery: true, EnableDatagrams: true}),
+		)
 		Expect(err).ToNot(HaveOccurred())
 		defer ln.Close()
 		go func() {
@@ -73,7 +77,7 @@ var _ = Describe("DPLPMTUD", func() {
 			context.Background(),
 			proxy.LocalAddr(),
 			getTLSClientConfig(),
-			getQuicConfig(nil),
+			getQuicConfig(&quic.Config{EnableDatagrams: true}),
 		)
 		Expect(err).ToNot(HaveOccurred())
 		defer conn.CloseWithError(0, "")
@@ -87,15 +91,27 @@ var _ = Describe("DPLPMTUD", func() {
 			Expect(err).ToNot(HaveOccurred())
 			Expect(data).To(Equal(PRDataLong))
 		}()
+		err = conn.SendDatagram(make([]byte, 2000))
+		Expect(err).To(BeAssignableToTypeOf(&quic.DatagramTooLargeError{}))
+		initialMaxDatagramSize := err.(*quic.DatagramTooLargeError).MaxDatagramPayloadSize
 		_, err = str.Write(PRDataLong)
 		Expect(err).ToNot(HaveOccurred())
 		str.Close()
 		Eventually(done, 20*time.Second).Should(BeClosed())
+		err = conn.SendDatagram(make([]byte, 2000))
+		Expect(err).To(BeAssignableToTypeOf(&quic.DatagramTooLargeError{}))
+		finalMaxDatagramSize := err.(*quic.DatagramTooLargeError).MaxDatagramPayloadSize
 
 		mx.Lock()
 		defer mx.Unlock()
 		fmt.Fprintf(GinkgoWriter, "max client packet size: %d, MTU: %d\n", maxPacketSizeClient, mtu)
+		fmt.Fprintf(GinkgoWriter, "max datagram size: initial: %d, final: %d\n", initialMaxDatagramSize, finalMaxDatagramSize)
 		fmt.Fprintf(GinkgoWriter, "max server packet size: %d, MTU: %d\n", maxPacketSizeServer, mtu)
 		Expect(maxPacketSizeClient).To(BeNumerically(">=", mtu-25))
+		const maxDiff = 40 // this includes the 21 bytes for the short header, 16 bytes for the encryption tag, and framing overhead
+		Expect(initialMaxDatagramSize).To(BeNumerically(">=", 1252-maxDiff))
+		Expect(finalMaxDatagramSize).To(BeNumerically(">=", maxPacketSizeClient-maxDiff))
+		// MTU discovery was disabled on the server side
+		Expect(maxPacketSizeServer).To(Equal(1252))
 	})
 })