This entry provides an overview of approaches to assessing speaking skills in language education within online collaborative learning environments, with attention to the role of artificial intelligence (AI) in supporting the development and evaluation of oral communication. It situates online collaborative speaking assessment within the broader field of computer-assisted language learning and outlines how digital platforms are used to design, implement, and assess speaking tasks across a range of educational contexts. While multilingual and international programmes in higher education, where English is often used as a Lingua Franca, constitute a prominent illustrative context, the discussion is not limited to this setting. Drawing on existing research and documented pedagogical practices, the entry offers an overview of key concepts, assessment practices, and illustrative examples, rather than reporting original empirical research, and highlights current challenges, methodological approaches, and emerging trends in AI-supported online speaking assessment.