People posses an innate capability to instinctively evaluate the trustworthiness of other people in their daily lives, and a hardwired tendency to react strongly if they feel betrayed. However, these capabilities do not work in the digital domain, for both obvious and not-so-obvious reasons. Therefore, something else is needed. In this paper we explore the prequisites and difficulties that are encountered when attempting to establish a bases for trust and trustworthy behaviour in the Internet, concentrating on the asset like nature of trustworthiness.