How to reset a CancellationToken properly?

You need to recreate the CancellationTokenSource – there is no way to “reset” this once you set it.

This could be as simple as:

private void Button_Click(object sender, RoutedEventArgs e)
{
    if (button.Content == "Start")
    {
        button.Content = "Stop";
        cts.Dispose(); // Clean up old token source....
        cts = new CancellationTokenSource(); // "Reset" the cancellation token source...
        DoWork(cts.Token);
    }
    else
    {
        button.Content = "Start";
        cts.Cancel();
    }
}