diff --git a/internal/command/wireguard/wireguard.go b/internal/command/wireguard/wireguard.go
index 76cb97eb8d..c87b5b2e21 100644
--- a/internal/command/wireguard/wireguard.go
+++ b/internal/command/wireguard/wireguard.go
@@ -13,6 +13,7 @@ import (
 	"github.com/superfly/flyctl/internal/config"
 	"github.com/superfly/flyctl/internal/flag"
 	"github.com/superfly/flyctl/internal/flyutil"
+	"github.com/superfly/flyctl/internal/metrics"
 	"github.com/superfly/flyctl/internal/render"
 	"github.com/superfly/flyctl/internal/state"
 	"github.com/superfly/flyctl/internal/wireguard"
@@ -62,21 +63,30 @@ func runWireguardWebsockets(ctx context.Context) error {
 	var (
 		configPath = state.ConfigFile(ctx)
 		err        error
+		enabled    bool
 	)
 	switch flag.FirstArg(ctx) {
 	case "enable":
+		enabled = true
 		viper.Set(flyctl.ConfigWireGuardWebsockets, true)
 		err = config.SetWireGuardWebsocketsEnabled(configPath, true)
 	case "disable":
+		enabled = false
 		viper.Set(flyctl.ConfigWireGuardWebsockets, false)
 		err = config.SetWireGuardWebsocketsEnabled(configPath, false)
 	default:
 		fmt.Fprintf(io.Out, "bad arg: flyctl wireguard websockets (enable|disable)\n")
+		return nil
 	}
 	if err != nil {
 		return errors.Wrap(err, "error saving config file")
 	}
 
+	// Send metrics about WebSocket configuration change
+	metrics.Send(ctx, "wireguard_websocket_config", map[string]interface{}{
+		"websocket_enabled": enabled,
+	})
+
 	tryKillingAgent := func() error {
 		client, err := agent.DefaultClient(ctx)
 		if err == agent.ErrAgentNotRunning {