diff --git a/lib/vnet/admin_process_darwin.go b/lib/vnet/admin_process_darwin.go
index 0465dd8e8aae5..9a7b789657a50 100644
--- a/lib/vnet/admin_process_darwin.go
+++ b/lib/vnet/admin_process_darwin.go
@@ -19,6 +19,7 @@ package vnet
 import (
 	"context"
 	"errors"
+	"os"
 	"time"
 
 	"github.com/gravitational/trace"
@@ -89,18 +90,21 @@ func RunDarwinAdminProcess(ctx context.Context, config daemon.Config) error {
 
 	g, ctx := errgroup.WithContext(ctx)
 	g.Go(func() error {
+		defer log.InfoContext(ctx, "Network stack terminated.")
 		if err := networkStack.run(ctx); err != nil {
 			return trace.Wrap(err, "running network stack")
 		}
 		return errors.New("network stack terminated")
 	})
 	g.Go(func() error {
+		defer log.InfoContext(ctx, "OS configuration loop exited.")
 		if err := osConfigurator.runOSConfigurationLoop(ctx); err != nil {
 			return trace.Wrap(err, "running OS configuration loop")
 		}
 		return errors.New("OS configuration loop terminated")
 	})
 	g.Go(func() error {
+		defer log.InfoContext(ctx, "Ping loop exited.")
 		tick := time.Tick(time.Second)
 		for {
 			select {
@@ -113,7 +117,27 @@ func RunDarwinAdminProcess(ctx context.Context, config daemon.Config) error {
 			}
 		}
 	})
-	return trace.Wrap(g.Wait(), "running VNet admin process")
+
+	done := make(chan error)
+	go func() {
+		done <- g.Wait()
+	}()
+
+	select {
+	case err := <-done:
+		return trace.Wrap(err, "running VNet admin process")
+	case <-ctx.Done():
+	}
+
+	select {
+	case err := <-done:
+		// network stack exited cleanly within timeout
+		return trace.Wrap(err, "running VNet admin process")
+	case <-time.After(10 * time.Second):
+		log.ErrorContext(ctx, "VNet admin process did not exit within 10 seconds, forcing shutdown.")
+		os.Exit(1)
+		return nil
+	}
 }
 
 func createTUNDevice(ctx context.Context) (tun.Device, string, error) {
diff --git a/lib/vnet/network_stack.go b/lib/vnet/network_stack.go
index 6c7d38ba14415..b2bf30d67d9fa 100644
--- a/lib/vnet/network_stack.go
+++ b/lib/vnet/network_stack.go
@@ -328,13 +328,16 @@ func (ns *networkStack) run(ctx context.Context) error {
 		// When the context is canceled for any reason (the caller or one of the other concurrent tasks may
 		// have canceled it) destroy everything and quit.
 		<-ctx.Done()
+		ns.slog.InfoContext(ctx, "Context canceled, beginning network stack shutdown.")
 
 		// In-flight connections should start terminating after closing [ns.destroyed].
 		close(ns.destroyed)
 
 		// Close the link endpoint and the TUN, this should cause [forwardBetweenTunAndNetstack] to terminate
 		// if it hasn't already.
+		ns.slog.InfoContext(ctx, "Closing link endpoint.")
 		ns.linkEndpoint.Close()
+		ns.slog.InfoContext(ctx, "Closing TUN device.")
 		err := trace.Wrap(ns.tun.Close(), "closing TUN device")
 
 		allErrors <- err
@@ -345,9 +348,11 @@ func (ns *networkStack) run(ctx context.Context) error {
 	_ = g.Wait()
 
 	// Wait for all connections and goroutines to clean themselves up.
+	ns.slog.InfoContext(ctx, "Waiting for all connections and goroutines to clean up.")
 	ns.wg.Wait()
 
 	// Now we can destroy the gVisor networking stack and wait for all its goroutines to terminate.
+	ns.slog.InfoContext(ctx, "Destroying networking stack.")
 	ns.stack.Destroy()
 
 	close(allErrors)
@@ -620,7 +625,9 @@ func forwardBetweenTunAndNetstack(ctx context.Context, tun tunDevice, linkEndpoi
 	g, ctx := errgroup.WithContext(ctx)
 	g.Go(func() error { return forwardNetstackToTUN(ctx, linkEndpoint, tun) })
 	g.Go(func() error { return forwardTUNtoNetstack(ctx, tun, linkEndpoint) })
-	return trace.Wrap(g.Wait())
+	err := g.Wait()
+	slog.DebugContext(ctx, "Finished forwarding IP packets between OS and VNet.")
+	return trace.Wrap(err)
 }
 
 func forwardNetstackToTUN(ctx context.Context, linkEndpoint *channel.Endpoint, tun tunDevice) error {