Nowadays when users navigate in internet they find lots of types of communication scattered across diverse sites. Due to the lack of users’ interests in advertisements, primarily caused by not matching their preferences, today’s advertisements have a low rate of success. Recently, owing to semantic web generation, some companies started to use personalized marketing in communication as a way to turn the conversions around and thus increase customer retention and loyalty. As a matter of fact, the retention and loyalty stages on the internet are, on average, the least crafted of the whole cycle. The customers’ conception of one-to-one marketing is quite ambiguous as they conceive that they need to be more efficient while shopping online but at the same time they feel stalked due to privacy concerns, and oversaturated with non-valuable information. The purpose of this paper is to explore from a holistic view online personalized communication strategies and how they can be implemented in order to increase customer satisfaction thus retaining customers and, in the long-term, gaining their loyalty. The main communication areas the study treats ranges from onsite the online store, where the company wants to sell the product, to offsite advertisements in websites, social media platforms and via email. In the empirical section, the study carried out a quantitative online survey to investigate customers’ perception and complete it with the literature. To answer the research questions, the study identified 19 hypotheses comprising of all primary aspects that define the exploration. The result could be gold dust for e-shop managers to help them maximize the marketing communication factor using personalization. The authors identified potential improvements to motivate customers to register in the online shop, whether communication channels are suited to implementing the strategy or not, and possible aspects to adapt in order to obtain maximal benefits. There were some limitations in terms of an analysis of the companies’ point of view and the necessity to analyze every communication channel more in depth as the study is an initial step.