diff --git a/server/leafnode.go b/server/leafnode.go
index a448c331..842e5a4c 100644
--- a/server/leafnode.go
+++ b/server/leafnode.go
@@ -508,13 +508,14 @@ func (s *Server) startLeafNodeAcceptLoop() {
 var credsRe = regexp.MustCompile(`\s*(?:(?:[-]{3,}[^\n]*[-]{3,}\n)(.+)(?:\n\s*[-]{3,}[^\n]*[-]{3,}\n))`)
 
 // Lock should be held entering here.
-func (c *client) sendLeafConnect(clusterName string, tlsRequired bool) error {
+func (c *client) sendLeafConnect(clusterName string, tlsRequired, headers bool) error {
 	// We support basic user/pass and operator based user JWT with signatures.
 	cinfo := leafConnectInfo{
 		TLS:     tlsRequired,
 		Name:    c.srv.info.ID,
 		Hub:     c.leaf.remote.Hub,
 		Cluster: clusterName,
+		Headers: headers,
 	}
 
 	// Check for credentials first, that will take precedence..
@@ -691,6 +692,7 @@ func (s *Server) createLeafNode(conn net.Conn, remote *leafNodeCfg) *client {
 		s.generateNonce(nonce[:])
 	}
 	clusterName := s.info.Cluster
+	headers := s.supportsHeaders()
 	s.mu.Unlock()
 
 	// Grab lock
@@ -825,7 +827,7 @@ func (s *Server) createLeafNode(conn net.Conn, remote *leafNodeCfg) *client {
 			}
 		}
 
-		if err := c.sendLeafConnect(clusterName, tlsRequired); err != nil {
+		if err := c.sendLeafConnect(clusterName, tlsRequired, headers); err != nil {
 			c.mu.Unlock()
 			c.closeConnection(ProtocolViolation)
 			return nil
@@ -888,7 +890,6 @@ func (s *Server) createLeafNode(conn net.Conn, remote *leafNodeCfg) *client {
 
 		// Leaf nodes will always require a CONNECT to let us know
 		// when we are properly bound to an account.
-		// The connection may have been closed
 		c.setAuthTimer(secondsToDuration(opts.LeafNode.AuthTimeout))
 	}
 
@@ -1161,6 +1162,7 @@ type leafConnectInfo struct {
 	Name    string `json:"name,omitempty"`
 	Hub     bool   `json:"is_hub,omitempty"`
 	Cluster string `json:"cluster,omitempty"`
+	Headers bool   `json:"headers,omitempty"`
 
 	// Just used to detect wrong connection attempts.
 	Gateway string `json:"gateway,omitempty"`
@@ -1194,11 +1196,18 @@ func (c *client) processLeafNodeConnect(s *Server, arg []byte, lang string) erro
 		return ErrWrongGateway
 	}
 
+	// Check if this server supports headers.
+	supportHeaders := c.srv.supportsHeaders()
+
 	c.mu.Lock()
 	// Leaf Nodes do not do echo or verbose or pedantic.
 	c.opts.Verbose = false
 	c.opts.Echo = false
 	c.opts.Pedantic = false
+	// This inbound connection will be marked as supporting headers if this server
+	// support headers and the remote has sent in the CONNECT protocol that it does
+	// support headers too.
+	c.headers = supportHeaders && proto.Headers
 
 	// If the other side has declared itself a hub, so we will take on the spoke role.
 	if proto.Hub {
diff --git a/test/leafnode_test.go b/test/leafnode_test.go
index c4d91486..25d974ea 100644
--- a/test/leafnode_test.go
+++ b/test/leafnode_test.go
@@ -4240,3 +4240,61 @@ func TestLeafNodeStreamAndShadowSubs(t *testing.T) {
 		t.Fatalf("Did not receive message: %v", err)
 	}
 }
+
+func TestLeafnodeHeaders(t *testing.T) {
+	srv, opts := runLeafServer()
+	defer srv.Shutdown()
+	leaf, _ := runSolicitLeafServer(opts)
+	defer leaf.Shutdown()
+
+	snc, err := nats.Connect(srv.ClientURL())
+	if err != nil {
+		t.Fatalf(err.Error())
+	}
+	defer snc.Close()
+	ssub, err := snc.SubscribeSync("test")
+	if err != nil {
+		t.Fatalf("subscribe failed: %s", err)
+	}
+
+	lnc, err := nats.Connect(leaf.ClientURL())
+	if err != nil {
+		t.Fatalf(err.Error())
+	}
+	defer lnc.Close()
+	lsub, err := lnc.SubscribeSync("test")
+	if err != nil {
+		t.Fatalf("subscribe failed: %s", err)
+	}
+	lnc.Flush()
+
+	checkLeafNodeConnected(t, srv)
+	checkLeafNodeConnected(t, leaf)
+	checkSubInterest(t, srv, "$G", "test", time.Second)
+
+	msg := nats.NewMsg("test")
+	msg.Header.Add("Test", "Header")
+	if len(msg.Header) == 0 {
+		t.Fatalf("msg header is empty")
+	}
+	err = snc.PublishMsg(msg)
+	if err != nil {
+		t.Fatalf(err.Error())
+	}
+
+	smsg, err := ssub.NextMsg(time.Second)
+	if err != nil {
+		t.Fatalf("next failed: %s", err)
+	}
+	if len(smsg.Header) == 0 {
+		t.Fatalf("server msgs header is empty")
+	}
+
+	lmsg, err := lsub.NextMsg(time.Second)
+	if err != nil {
+		t.Fatalf("next failed: %s", err)
+	}
+	if len(lmsg.Header) == 0 {
+		t.Fatalf("leaf msg header is empty")
+	}
+}