diff --git a/cmd/fleetctl/preview.go b/cmd/fleetctl/preview.go
index a611af7ca1..07f9d94cd4 100644
--- a/cmd/fleetctl/preview.go
+++ b/cmd/fleetctl/preview.go
@@ -250,6 +250,12 @@ Use the stop and reset subcommands to manage the server and dependencies once st
 				return errors.Wrap(err, "downloading orbit and osqueryd")
 			}
 
+			// Give it a bit of time so the current device is the one with id 1
+			fmt.Println("Waiting for current host to enroll...")
+			if err := waitFirstHost(client); err != nil {
+				return errors.Wrap(err, "wait for current host")
+			}
+
 			fmt.Println("Starting simulated hosts...")
 			cmd = exec.Command("docker-compose", "up", "-d", "--remove-orphans")
 			cmd.Dir = filepath.Join(previewDir, "osquery")
@@ -409,6 +415,30 @@ func waitStartup() error {
 	return nil
 }
 
+func waitFirstHost(client *service.Client) error {
+	retryStrategy := backoff.NewExponentialBackOff()
+	retryStrategy.MaxInterval = 1 * time.Second
+
+	if err := backoff.Retry(
+		func() error {
+			hosts, err := client.GetHosts("")
+			if err != nil {
+				return err
+			}
+			if len(hosts) == 0 {
+				return errors.New("no hosts yet")
+			}
+
+			return nil
+		},
+		retryStrategy,
+	); err != nil {
+		return errors.Wrap(err, "checking host count")
+	}
+
+	return nil
+}
+
 func checkDocker() error {
 	// Check installed
 	if _, err := exec.LookPath("docker"); err != nil {