diff --git a/p2p/discover/v5_udp.go b/p2p/discover/v5_udp.go
index 48256ea4de..00428a0985 100644
--- a/p2p/discover/v5_udp.go
+++ b/p2p/discover/v5_udp.go
@@ -55,6 +55,8 @@ type codecV5 interface {
 	// Decode decodes a packet. It returns a *v5wire.Unknown packet if decryption fails.
 	// The *enode.Node return value is non-nil when the input contains a handshake response.
 	Decode([]byte, string) (enode.ID, *enode.Node, v5wire.Packet, error)
+
+	CurrentChallenge(enode.ID, string) *v5wire.Whoareyou
 }
 
 // UDPv5 is the implementation of protocol version 5.
@@ -774,6 +776,19 @@ func (t *UDPv5) handle(p v5wire.Packet, fromID enode.ID, fromAddr netip.AddrPort
 
 // handleUnknown initiates a handshake by responding with WHOAREYOU.
 func (t *UDPv5) handleUnknown(p *v5wire.Unknown, fromID enode.ID, fromAddr netip.AddrPort) {
+	currentChallenge := t.codec.CurrentChallenge(fromID, fromAddr.String())
+	if currentChallenge != nil {
+		// This case happens when the sender issues multiple concurrent requests.
+		// Since we only support one in-progress handshake at a time, we need to tell
+		// them which handshake attempt they need to complete. We tell them to use the
+		// existing handshake attempt since the response to that one might still be in
+		// transit.
+		t.log.Warn("Repeating discv5 handshake challenge", "id", fromID, "addr", fromAddr)
+		t.sendResponse(fromID, fromAddr, currentChallenge)
+		return
+	}
+
+	// Send a fresh challenge.
 	challenge := &v5wire.Whoareyou{Nonce: p.Nonce}
 	crand.Read(challenge.IDNonce[:])
 	if n := t.getNode(fromID); n != nil {
diff --git a/p2p/discover/v5_udp_test.go b/p2p/discover/v5_udp_test.go
index 8631b918ff..7bb313d942 100644
--- a/p2p/discover/v5_udp_test.go
+++ b/p2p/discover/v5_udp_test.go
@@ -717,6 +717,10 @@ func (c *testCodec) Encode(toID enode.ID, addr string, p v5wire.Packet, _ *v5wir
 	return frame, authTag, err
 }
 
+func (c *testCodec) CurrentChallenge(enode.ID, string) *v5wire.Whoareyou {
+	return nil
+}
+
 func (c *testCodec) Decode(input []byte, addr string) (enode.ID, *enode.Node, v5wire.Packet, error) {
 	frame, p, err := c.decodeFrame(input)
 	if err != nil {
diff --git a/p2p/discover/v5wire/encoding.go b/p2p/discover/v5wire/encoding.go
index 904a3ddec6..e50b7cd16d 100644
--- a/p2p/discover/v5wire/encoding.go
+++ b/p2p/discover/v5wire/encoding.go
@@ -245,6 +245,12 @@ func (c *Codec) EncodeRaw(id enode.ID, head Header, msgdata []byte) ([]byte, err
 	return c.buf.Bytes(), nil
 }
 
+// CurrentChallenge returns the latest challenge sent to the given node.
+// This will return non-nil while a handshake is in progress.
+func (c *Codec) CurrentChallenge(id enode.ID, addr string) *Whoareyou {
+	return c.sc.getHandshake(id, addr)
+}
+
 func (c *Codec) writeHeaders(head *Header) {
 	c.buf.Reset()
 	c.buf.Write(head.IV[:])