The paper examines the role of context in reading unpointed Hebrew, demonstrating the changing nature of reliance on context during the course of reading acquisition. We analyze the reading-aloud of sentences with heterographic-homographic ambiguity, aiming to shed light on the development of ambiguity resolution processes in typically developing schoolaged and adult populations. 171 Hebrew-speaking children and adolescents in seven age/schooling groups (beginning and end of second grade, third, fourth, seventh, and eleventh grade), and a group of adults, participated in the study. Using homographic garden-path and non-Garden-path sentences, we demonstrate the cumulative effect of context as well as processes of monitoring cum reanalysis. Two hypotheses are borne out in the present research: First, context effect is inherent to reading; it is present throughout all age/grade groups, becoming more efficient with age/grade level. Second, monitoring and reanalysis lag far behind context effects, appearing only as age and reading experience increase.