This article describes an attempt to adopt dynamic assessment (DA) methods in classroom speaking assessments. The study reported in this article focused on four particular applications of dynamic speaking assessment (DSA). The first, "mediated assistance" (MA), involves interaction between an assistor and a learner to reveal problems in spoken performance. The second DSA approach is to discover learners' ability to transfer what they have already internalized to novel problems. This "transfer-of-learning" (TOL) ability to overcome performance problems also represents the primary means of assessing genuine development. Vygotsky's (1986) "zone of proximal development" (ZPD) is the third DSA application. However, the proximal zone between more and less competent individuals is not the only construct under observation. The same developmental and problem-solving ability between individuals can also become collective and interconnected in groups. A group ZPD (GZPD) breaks from the cognitively biased preoccupation with the autonomous individual and shifts the focus to the sociocultural nature of the ZPD. The final DSA approach is "collaborative engagement" (CE), which involves diagnosing problem areas during DSA, especially when there has not been indication of TOL or the internalization of any cognitive tools. Data suggest that TOL in the form of role-plays of graduated difficulty is a genuine means of assessing development of second language acquisition. Pairing and sequencing learners according to their levels and allowing them to observe previous pairs (i.e., a GZPD) may interconnect their performance, improve DSA performance, and reduce variation in performance. MA data suggest it has significant cumulative improvement not only in learners' speaking performance but in their reciprocity (primarily in the form of recasts). (Contains 2 tables and 1 figure.)