diff --git a/src/fruity/device-monitor-macos.vala b/src/fruity/device-monitor-macos.vala
index 974fd7680..24ecf96b0 100644
--- a/src/fruity/device-monitor-macos.vala
+++ b/src/fruity/device-monitor-macos.vala
@@ -246,6 +246,12 @@ namespace Frida.Fruity {
 			}
 		}
 
+		public int64 opened_at {
+			get {
+				return _opened_at;
+			}
+		}
+
 		public Darwin.Xpc.Uuid? assertion_identifier {
 			get {
 				return _assertion_identifier;
@@ -256,6 +262,7 @@ namespace Frida.Fruity {
 		private Darwin.Xpc.Uuid? _assertion_identifier;
 		private InetAddress? tunnel_device_address;
 		private DiscoveryService? _discovery;
+		private int64 _opened_at = -1;
 
 		public MacOSTunnel (XpcClient pairing_device) {
 			this.pairing_device = pairing_device;
@@ -275,6 +282,8 @@ namespace Frida.Fruity {
 			r.body.set_int64 ("flags", 0);
 			var response = yield pairing_device.request (r.message, cancellable);
 
+			_opened_at = get_monotonic_time ();
+
 			var reader = new XpcObjectReader (response);
 			reader.read_member ("response");
 
diff --git a/src/fruity/device-monitor.vala b/src/fruity/device-monitor.vala
index adf41075c..2448615de 100644
--- a/src/fruity/device-monitor.vala
+++ b/src/fruity/device-monitor.vala
@@ -492,6 +492,10 @@ namespace Frida.Fruity {
 			get;
 		}
 
+		public abstract int64 opened_at {
+			get;
+		}
+
 		public abstract async void close (Cancellable? cancellable) throws IOError;
 		public abstract async IOStream open_tcp_connection (uint16 port, Cancellable? cancellable) throws Error, IOError;
 	}
@@ -1635,9 +1639,16 @@ namespace Frida.Fruity {
 			}
 		}
 
+		public int64 opened_at {
+			get {
+				return _opened_at;
+			}
+		}
+
 		private UsbNcmDriver? ncm;
 		private TunnelConnection? tunnel_connection;
 		private DiscoveryService? _discovery_service;
+		private int64 _opened_at = -1;
 
 		public PortableUsbTunnel (UsbDevice device, NcmPeer peer, PairingStore store) {
 			Object (
@@ -1670,6 +1681,8 @@ namespace Frida.Fruity {
 			TunnelConnection tc = yield pairing_service.open_tunnel (ncm_peer.ip, netstack, cancellable);
 			tc.closed.connect (on_tunnel_connection_close);
 
+			_opened_at = get_monotonic_time ();
+
 			var rsd_endpoint = (InetSocketAddress) Object.new (typeof (InetSocketAddress),
 				address: tc.remote_address,
 				port: tc.remote_rsd_port,
@@ -1831,8 +1844,15 @@ namespace Frida.Fruity {
 			}
 		}
 
+		public int64 opened_at {
+			get {
+				return _opened_at;
+			}
+		}
+
 		private TunnelConnection? tunnel_connection;
 		private DiscoveryService? _discovery_service;
+		private int64 _opened_at = -1;
 
 		private const uint PAIRING_CONNECTION_TIMEOUT = 2000;
 
@@ -1854,6 +1874,8 @@ namespace Frida.Fruity {
 
 			TunnelConnection tc = yield pairing_service.open_tunnel (endpoint.get_address (), netstack, cancellable);
 
+			_opened_at = get_monotonic_time ();
+
 			var rsd_endpoint = (InetSocketAddress) Object.new (typeof (InetSocketAddress),
 				address: tc.remote_address,
 				port: tc.remote_rsd_port,
diff --git a/src/fruity/fruity-host-session.vala b/src/fruity/fruity-host-session.vala
index fe2c6df4c..d85be1483 100644
--- a/src/fruity/fruity-host-session.vala
+++ b/src/fruity/fruity-host-session.vala
@@ -1087,8 +1087,7 @@ namespace Frida {
 
 			DBusConnection? connection = null;
 			try {
-				var channel =
-					yield device.open_tcp_channel (DEFAULT_CONTROL_PORT.to_string (), ALLOW_ANY_TRANSPORT, cancellable);
+				var channel = yield connect_to_remote_server (cancellable);
 
 				IOStream stream = channel.stream;
 				WebServiceTransport transport = PLAIN;
@@ -1157,6 +1156,51 @@ namespace Frida {
 			}
 		}
 
+		private async Fruity.TcpChannel connect_to_remote_server (Cancellable? cancellable) throws Error, IOError {
+			var tunnel = yield device.find_tunnel (cancellable);
+			bool tunnel_recently_opened = tunnel != null && get_monotonic_time () - tunnel.opened_at < 1000000;
+
+			uint delays[] = { 0, 50, 250 };
+			uint max_attempts = tunnel_recently_opened ? delays.length : 1;
+			var main_context = MainContext.ref_thread_default ();
+
+			Error? pending_error = null;
+			for (uint attempts = 0; attempts != max_attempts; attempts++) {
+				uint delay = delays[attempts];
+				if (delay != 0) {
+					var timeout_source = new TimeoutSource (delay);
+					timeout_source.set_callback (connect_to_remote_server.callback);
+					timeout_source.attach (main_context);
+
+					var cancel_source = new CancellableSource (cancellable);
+					cancel_source.set_callback (connect_to_remote_server.callback);
+					cancel_source.attach (main_context);
+
+					yield;
+
+					cancel_source.destroy ();
+					timeout_source.destroy ();
+
+					if (cancellable.is_cancelled ())
+						break;
+				}
+
+				bool is_last_attempt = attempts == max_attempts - 1;
+				var open_flags = is_last_attempt
+					? Fruity.OpenTcpChannelFlags.ALLOW_ANY_TRANSPORT
+					: Fruity.OpenTcpChannelFlags.ALLOW_TUNNEL;
+
+				try {
+					return yield device.open_tcp_channel (DEFAULT_CONTROL_PORT.to_string (), open_flags, cancellable);
+				} catch (Error e) {
+					pending_error = e;
+					if (!(e is Error.SERVER_NOT_RUNNING))
+						break;
+				}
+			}
+			throw pending_error;
+		}
+
 		private void attach_remote_server (RemoteServer server) {
 			server.connection.on_closed.connect (on_remote_connection_closed);