This thesis investigates online newspapers in Lebanon, and their adoption of, and adaptation to, new technologies in 2008 and 2014. The study examines two online newspapers that descend from a print version: Annaharonline and Aldiyaronline, and a born-on-the-web newspaper, Elnashra. The data obtained are used to examine their rationale and development processes, communication routines and the use of interactive features. This thesis employed three research methods: ethnographic observations, ethnographic interviews, and content analysis. The observation of the three newspaper newsrooms and the interviews with their editors journalists were conducted in Lebanon. Qualitative and quantitative content analysis of the interactive features was carried out in order to examine the extent and format of readers’ comments on the news, and the utilisation of multimedia in the three newspapers. The Diffusion of Innovation theory (DOI) was used as the main analytical framework for this research, which revealed that the three Lebanese online newspapers remained in the ‘trial stage’ for an extended period; although the Lebanese newspapers were among the first in the Middle East to adopt an online version, they were tardy in adapting to this new technology - many incidents, mainly the turbulent political and economic situation, interfered with the adoption and decision processes; moreover, the flow of global technology, the competition in media industry, the Lebanese Diaspora, the Arab revolts and social media were other significant factors in the slow development of online newspapers in Lebanon. This research suggests that the editors-in-chief of the Lebanese online newspapers fell between the ‘late majority’ and the ‘laggards’ categories, which are understood to deliberate for a protracted phase, before they make a decision to adopt and adapt. This study concluded that the Lebanese online newspapers followed the same news delivery policy as their print editions by publishing, practically unchanged, the print version of their articles on to their websites; online journalists from two of the three studied newspapers selected the news items from their print newspapers and other multimedia sources, rather than creating them; this practice met fixed print deadlines, but did not fully exploit the flexibility of online newspapers, and therefore, the advantages of the Internet interactive features, such as the readers’ comments on the news items posted on the websites, were undervalued. The findings in this research concluded that, although the Lebanese online newspapers under study had upgraded some interactive properties to their websites, they were less organised than the born-on-the-web version which employed dedicated and trained online journalists, rather than charging untrained print copy journalists with additional duties.