Customer loyalty has become a top priority for e-tailers and millions of dollars are invested each year in electronic Customer Relationship Management (e-CRM). However, the effectiveness of e-CRM in improving relationship quality and enhancing actual customer patronage behaviors is still questioning: no research has examined the links between actual customer patronage behavior and customers’ perceptions of the e-tailer’s marketing activities, tools and techniques delivered over the Internet. To fill this gap, our research crosses customers’ perceptions (e-CRM drivers) and relational constructs (trust and relationship commitment) collected through a questionnaire with actual customer patronage behavior extracted from two e-tailers’ databases. We then demonstrate that e-CRM activities can improve or damage relationship quality (trust and or relationship commitment) and then, through them, affect repeat purchase behavior. Taking also into account the reality of emailing campaigns, we note that company-initiated emails are significantly less effective than customer-initiated emails, i.e. messages tailored automatically to the customers (trigger based email campaigns). Thus, this research supports a relational view of e-tailing and suggests using technologies which effectively improve relationship quality and empower customers (customer-initiated contact).