Track user connections across clusters (#32688)

Ensure that `proxy_ssh_sessions_total` is incremented in both the
root and the leaf cluster if a session to a node in the leaf cluster
is established through the root cluster. This now also prevents
leaf clusters from terminating during a graceful shutdown if there
is an active connection that was created from the root.

Fixes #32605.

lib/proxy/router.go

@@ -76,24 +76,24 @@ func init() {
 	metrics.RegisterPrometheusCollectors(proxiedSessions, failedConnectingToNode, connectingToNode)
 }
 
-// proxiedMetricConn wraps [net.Conn] opened by
+// ProxiedMetricConn wraps [net.Conn] opened by
 // the [Router] so that the proxiedSessions counter
 // can be decremented when it is closed.
-type proxiedMetricConn struct {
+type ProxiedMetricConn struct {
 	// once ensures that proxiedSessions is only decremented
 	// a single time per [net.Conn]
 	once sync.Once
 	net.Conn
 }
 
-// newProxiedMetricConn increments proxiedSessions and creates
-// a proxiedMetricConn that defers to the provided [net.Conn].
-func newProxiedMetricConn(conn net.Conn) *proxiedMetricConn {
+// NewProxiedMetricConn increments proxiedSessions and creates
+// a ProxiedMetricConn that defers to the provided [net.Conn].
+func NewProxiedMetricConn(conn net.Conn) *ProxiedMetricConn {
 	proxiedSessions.Inc()
-	return &proxiedMetricConn{Conn: conn}
+	return &ProxiedMetricConn{Conn: conn}
 }
 
-func (c *proxiedMetricConn) Close() error {
+func (c *ProxiedMetricConn) Close() error {
 	c.once.Do(proxiedSessions.Dec)
 	return trace.Wrap(c.Conn.Close())
 }
@@ -313,7 +313,7 @@ func (r *Router) DialHost(ctx context.Context, clientSrcAddr, clientDstAddr net.
 		return nil, trace.Wrap(err)
 	}
 
-	return newProxiedMetricConn(conn), trace.Wrap(err)
+	return NewProxiedMetricConn(conn), trace.Wrap(err)
 }
 
 // getRemoteCluster looks up the provided clusterName to determine if a remote site exists with
@@ -475,7 +475,7 @@ func (r *Router) DialSite(ctx context.Context, clusterName string, clientSrcAddr
 		return nil, trace.Wrap(err)
 	}
 
-	return newProxiedMetricConn(conn), trace.Wrap(err)
+	return NewProxiedMetricConn(conn), trace.Wrap(err)
 }
 
 // GetSiteClient returns an auth client for the provided cluster.

lib/reversetunnel/agentpool.go

@@ -515,7 +515,7 @@ func (p *AgentPool) getVersion(ctx context.Context) (string, error) {
 
 // transport creates a new transport instance.
 func (p *AgentPool) transport(ctx context.Context, channel ssh.Channel, requests <-chan *ssh.Request, conn sshutils.Conn) *transport {
-	return &transport{
+	t := &transport{
 		closeContext:         ctx,
 		component:            p.Component,
 		localClusterName:     p.LocalCluster,
@@ -532,6 +532,17 @@ func (p *AgentPool) transport(ctx context.Context, channel ssh.Channel, requests
 		proxySigner:          p.PROXYSigner,
 		forwardClientAddress: true,
 	}
+
+	// If the AgentPool is being used for Proxy to Proxy communication between two clusters, then
+	// we check if the reverse tunnel server is capable of tracking user connections. This allows
+	// the leaf proxy to track sessions that are initiated via the root cluster. Without providing
+	// the user tracker the leaf cluster metrics will be incorrect and graceful shutdown will not
+	// wait for user sessions to be terminated prior to proceeding with the shutdown operation.
+	if p.IsRemoteCluster && p.ReverseTunnelServer != nil {
+		t.trackUserConnection = p.ReverseTunnelServer.TrackUserConnection
+	}
+
+	return t
 }
 
 // agentPoolRuntimeConfig contains configurations dynamically set and updated

lib/reversetunnel/srv.go

@@ -1084,6 +1084,13 @@ func (s *server) rejectRequest(ch ssh.NewChannel, reason ssh.RejectionReason, ms
 	}
 }
 
+// TrackUserConnection tracks a user connection that should prevent
+// the server from being terminated if active. The returned function
+// should be called when the connection is terminated.
+func (s *server) TrackUserConnection() (release func()) {
+	return s.srv.TrackUserConnection()
+}
+
 // newRemoteSite helper creates and initializes 'remoteSite' instance
 func newRemoteSite(srv *server, domainName string, sconn ssh.Conn) (*remoteSite, error) {
 	connInfo, err := types.NewTunnelConnection(

lib/reversetunnel/transport.go

@@ -36,6 +36,7 @@ import (
 	"github.com/gravitational/teleport/api/utils/sshutils"
 	"github.com/gravitational/teleport/lib/auth"
 	"github.com/gravitational/teleport/lib/multiplexer"
+	"github.com/gravitational/teleport/lib/proxy"
 	"github.com/gravitational/teleport/lib/reversetunnelclient"
 	"github.com/gravitational/teleport/lib/utils"
 )
@@ -93,6 +94,9 @@ type transport struct {
 	// preventing users connecting to the proxy tunnel listener spoofing their address; but we are still able to
 	// correctly propagate client address in reverse tunnel agents of nodes/services.
 	forwardClientAddress bool
+
+	// trackUserConnection is an optional mechanism used to count active user sessions.
+	trackUserConnection func() (release func())
 }
 
 // start will start the transporting data over the tunnel. This function will
@@ -246,6 +250,10 @@ func (p *transport) start() {
 		// tunnel from the SSH node by dreq.ServerID. We'll need to forward
 		// dreq.Address as well.
 		directAddress = dreq.Address
+
+		if p.trackUserConnection != nil {
+			defer p.trackUserConnection()()
+		}
 	default:
 		// Not a special address; could be empty.
 		directAddress = dreq.Address
@@ -395,6 +403,11 @@ func (p *transport) getConn(addr string, r *sshutils.DialReq) (net.Conn, bool, e
 	}
 
 	p.log.Debugf("Returning connection dialed through tunnel with server ID %v.", r.ServerID)
+
+	if r.ConnType == types.NodeTunnel {
+		return proxy.NewProxiedMetricConn(conn), true, nil
+	}
+
 	return conn, true, nil
 }
 

lib/reversetunnelclient/api.go

@@ -158,6 +158,10 @@ type Server interface {
 	Wait(ctx context.Context)
 	// GetProxyPeerClient returns the proxy peer client
 	GetProxyPeerClient() *peer.Client
+	// TrackUserConnection tracks a user connection that should prevent
+	// the server from being terminated if active. The returned function
+	// should be called when the connection is terminated.
+	TrackUserConnection() (release func())
 }
 
 const (

lib/service/service.go

@@ -4661,12 +4661,12 @@ func (process *TeleportProcess) initProxyEndpoint(conn *Connector) error {
 		// really guaranteed to be capable to serve new requests if we're
 		// halfway through a shutdown, and double closing a listener is fine.
 		listeners.Close()
-		rcWatcher.Close()
 		if payload == nil {
 			log.Infof("Shutting down immediately.")
 			if tsrv != nil {
 				warnOnErr(tsrv.Close(), log)
 			}
+			warnOnErr(rcWatcher.Close(), log)
 			if proxyServer != nil {
 				warnOnErr(proxyServer.Close(), log)
 			}
@@ -4713,6 +4713,7 @@ func (process *TeleportProcess) initProxyEndpoint(conn *Connector) error {
 			if tsrv != nil {
 				warnOnErr(tsrv.Shutdown(ctx), log)
 			}
+			warnOnErr(rcWatcher.Close(), log)
 			if proxyServer != nil {
 				warnOnErr(proxyServer.Shutdown(), log)
 			}

lib/sshutils/server.go

@@ -441,6 +441,17 @@ func (s *Server) trackUserConnections(delta int32) int32 {
 	return atomic.AddInt32(&s.userConns, delta)
 }
 
+// TrackUserConnection tracks a user connection that should prevent
+// the server from being terminated if active. The returned function
+// should be called when the connection is terminated.
+func (s *Server) TrackUserConnection() (release func()) {
+	s.trackUserConnections(1)
+
+	return sync.OnceFunc(func() {
+		s.trackUserConnections(-1)
+	})
+}
+
 // ActiveConnections returns the number of connections that are
 // being served.
 func (s *Server) ActiveConnections() int32 {