diff --git a/server/reload.go b/server/reload.go
index aff64ccd..7058417f 100644
--- a/server/reload.go
+++ b/server/reload.go
@@ -413,7 +413,9 @@ func (r *routesOption) Apply(server *Server) {
 	}
 
 	// Add routes.
+	server.mu.Lock()
 	server.solicitRoutes(r.add)
+	server.mu.Unlock()
 
 	server.Noticef("Reloaded: cluster routes")
 }
diff --git a/server/route.go b/server/route.go
index 0ed56a48..c37bf682 100644
--- a/server/route.go
+++ b/server/route.go
@@ -1305,6 +1305,7 @@ func (s *Server) createRoute(conn net.Conn, rURL *url.URL) *client {
 	authRequired := s.routeInfo.AuthRequired
 	tlsRequired := s.routeInfo.TLSRequired
 	clusterName := s.info.Cluster
+	tlsName := s.routeTLSName
 	s.mu.Unlock()
 
 	// Grab lock
@@ -1329,8 +1330,13 @@ func (s *Server) createRoute(conn net.Conn, rURL *url.URL) *client {
 			tlsConfig = tlsConfig.Clone()
 		}
 		// Perform (server or client side) TLS handshake.
-		if _, err := c.doTLSHandshake("route", didSolicit, rURL, tlsConfig, _EMPTY_, opts.Cluster.TLSTimeout, opts.Cluster.TLSPinnedCerts); err != nil {
+		if resetTLSName, err := c.doTLSHandshake("route", didSolicit, rURL, tlsConfig, tlsName, opts.Cluster.TLSTimeout, opts.Cluster.TLSPinnedCerts); err != nil {
 			c.mu.Unlock()
+			if resetTLSName {
+				s.mu.Lock()
+				s.routeTLSName = _EMPTY_
+				s.mu.Unlock()
+			}
 			return nil
 		}
 	}
@@ -1897,7 +1903,24 @@ func (c *client) isSolicitedRoute() bool {
 	return c.kind == ROUTER && c.route != nil && c.route.didSolicit
 }
 
+// Save the first hostname found in route URLs. This will be used in gossip mode
+// when trying to create a TLS connection by setting the tlsConfig.ServerName.
+// Lock is held on entry
+func (s *Server) saveRouteTLSName() {
+	var tlsName string
+	for _, u := range s.getOpts().Routes {
+		if tlsName == _EMPTY_ && net.ParseIP(u.Hostname()) == nil {
+			tlsName = u.Hostname()
+		}
+	}
+	s.routeTLSName = tlsName
+}
+
+// Start connection process to provided routes. Each route connection will
+// be started in a dedicated go routine.
+// Lock is held on entry
 func (s *Server) solicitRoutes(routes []*url.URL) {
+	s.saveRouteTLSName()
 	for _, r := range routes {
 		route := r
 		s.startGoRoutine(func() { s.connectToRoute(route, true, true) })
diff --git a/server/routes_test.go b/server/routes_test.go
index ed3405ed..1c9c205e 100644
--- a/server/routes_test.go
+++ b/server/routes_test.go
@@ -1670,3 +1670,60 @@ func TestRouteSolicitedReconnectsEvenIfImplicit(t *testing.T) {
 		// OK
 	}
 }
+
+func TestRouteSaveTLSName(t *testing.T) {
+	c1Conf := createConfFile(t, []byte(`
+		port: -1
+		cluster {
+			name: "abc"
+			port: -1
+			tls {
+				cert_file: '../test/configs/certs/server-noip.pem'
+				key_file: '../test/configs/certs/server-key-noip.pem'
+				ca_file: '../test/configs/certs/ca.pem'
+			}
+		}
+	`))
+	defer removeFile(t, c1Conf)
+	s1, o1 := RunServerWithConfig(c1Conf)
+	defer s1.Shutdown()
+
+	c2And3Conf := createConfFile(t, []byte(fmt.Sprintf(`
+		port: -1
+		cluster {
+			name: "abc"
+			port: -1
+			routes: ["nats://localhost:%d"]
+			tls {
+				cert_file: '../test/configs/certs/server-noip.pem'
+				key_file: '../test/configs/certs/server-key-noip.pem'
+				ca_file: '../test/configs/certs/ca.pem'
+			}
+		}
+	`, o1.Cluster.Port)))
+	defer removeFile(t, c2And3Conf)
+	s2, _ := RunServerWithConfig(c2And3Conf)
+	defer s2.Shutdown()
+
+	checkClusterFormed(t, s1, s2)
+
+	s3, _ := RunServerWithConfig(c2And3Conf)
+	defer s3.Shutdown()
+
+	checkClusterFormed(t, s1, s2, s3)
+
+	// Do a reload of s2 and close the route connections and make sure it
+	// reconnects properly.
+	err := s2.Reload()
+	require_NoError(t, err)
+
+	s2.mu.RLock()
+	for _, r := range s2.routes {
+		r.mu.Lock()
+		r.nc.Close()
+		r.mu.Unlock()
+	}
+	s2.mu.RUnlock()
+
+	checkClusterFormed(t, s1, s2, s3)
+}
diff --git a/server/server.go b/server/server.go
index 607958a9..c6e18980 100644
--- a/server/server.go
+++ b/server/server.go
@@ -152,6 +152,7 @@ type Server struct {
 	routeInfoJSON       []byte
 	routeResolver       netResolver
 	routesToSelf        map[string]struct{}
+	routeTLSName        string
 	leafNodeListener    net.Listener
 	leafNodeListenerErr error
 	leafNodeInfo        Info