In this article, we studied the developmental trajectories of three teachers as they integrated GroupScribbles (GS) technology in their classroom lessons over a semester period of about 5 months. Coherency diagrams were used to capture the complex interplay of a teacher's knowledge (K), goals (G) and beliefs (B) in leveraging technology effectively in the classroom. The degree of coherency between the KGB region and the affordances of the technology provided an indication of the teacher's developmental progression through the initiation, implementation and maturation phases of using technology in the classroom. Our findings reveal that a low coherency state at the initial stage not only has a high tendency for single regression to happen but also a double regression, when further triggered by certain factors. Dominant stagnation among the low coherency states throughout the initial and implementation phases increases the difficulty of upward transition to high coherency states. Implications are drawn as to the importance of ensuring high coherency during the initial phase where opportunities for synergy between a teacher's KGBs and the affordances of the technology should be created as early as possible to minimize regression.