In this short paper, we investigate the problems with the employment of the notion of freedom and voluntariness in libertarianism. We pretend to demonstrate that these two, as conceived of by libertarians, figure in as the main issue when it comes to justifying its major institutions, say: bequeathing, gifts, transactions (or what they label as “voluntary transfer”). The difficulty here boils down to the fact that a purely rights-based idea of freedom and voluntariness, the pretentions of Nozick notwithstanding, cannot do alone, since it is the consideration whether we do something (e.g. bequeath, donate etc.) voluntarily (or freely) (in a non-moralized sense) that could account for the rights redistribution. Therefore, it seems that – at least sometimes – the notion of voluntariness (or freedom) is prior to the notion of rights.