diff --git a/libtailscale/backend.go b/libtailscale/backend.go
index 21eea06..afe7f46 100644
--- a/libtailscale/backend.go
+++ b/libtailscale/backend.go
@@ -225,6 +225,8 @@ func (a *App) runBackend(ctx context.Context) error {
 				if err := b.updateTUN(cfg.rcfg, cfg.dcfg); err != nil {
 					a.closeVpnService(err, b)
 				}
+			} else {
+				b.logger.Logf("Update TUN not called")
 			}
 		case s := <-onDisconnect:
 			b.CloseTUNs()
diff --git a/libtailscale/interfaces.go b/libtailscale/interfaces.go
index 6460c9f..7aaaf18 100644
--- a/libtailscale/interfaces.go
+++ b/libtailscale/interfaces.go
@@ -166,6 +166,7 @@ type InputStream interface {
 // of various state changes.
 
 func RequestVPN(service IPNService) {
+	log.Printf("VPN requested")
 	onVPNRequested <- service
 }
 
diff --git a/libtailscale/net.go b/libtailscale/net.go
index 43d90da..0405316 100644
--- a/libtailscale/net.go
+++ b/libtailscale/net.go
@@ -207,6 +207,7 @@ func (b *backend) updateTUN(rcfg *router.Config, dcfg *dns.OSConfig) error {
 	b.logger.Logf("updateTUN: established VPN")
 
 	if parcelFD == nil {
+		b.logger.Logf("updateTUN: could not establish VPN because builder.Establish returned a nil ParcelFileDescriptor")
 		return errVPNNotPrepared
 	}