In today’s information society it is critical to use computer-mediated communication effectively. This article explores whether the highly recognized face-to-face communication concept “active listening” can also be applied to online settings. Demanding verbal and nonverbal skills, this way of communication improves mutual understanding by using techniques like paraphrasing. For instance, it avoids misunderstandings and in conflicts it increases chances to find a joint solution. The presented study investigates whether “active listening” is effective in written online communication, which is a novel asset. Focusing on instant messaging and e-mail, we examined both settings’ capacities and differences. Qualitative analysis based on a unique data set including log files and written user reactions on online “active listening” activities, reveals that “active listening” is possible in online communication, although a face-to -face setting is preferred due to a number of constraints imposed by online media. Results show that, while there are limitations to expressing empathy in online settings, the latter offer valuable opportunities that face-to-face conversations tend to lack. For instance, it appears that online media leave control with a communicator by allowing to completely verbalize thoughts before responding. Our results provide preliminary support that even newcomers to the concept can benefit from using active listening techniques in their online communication.