This study focuses on the stability of dyslexia status from Grade 2 to Grade 8 in four groups: (a) no dyslexia in either grade (no-dyslexia, n = 127); (b) no dyslexia in Grade 2 but dyslexia in Grade 8 (late-emerging, n = 18); (c) dyslexia in Grade 2 but not in Grade 8 (resolving, n = 15); and (d) dyslexia in both grades (persistent-dyslexia, n = 22). We examined group differences from age 3.5 to age 14 in (a) reading, vocabulary, phonology, letter knowledge, rapid naming, IQ, verbal memory; (b) familial and environmental risk and supportive factors; and (c) parental skills in reading, phonology, rapid naming, verbal memory, and vocabulary. Our findings showed group differences both in reading and cognitive skills of children as well as their parents. Parental education, book-reading frequency, and children’s IQ, however, did not differentiate the groups. The children in the persistent-dyslexia group exhibited widespread language and cognitive deficits across development. Those in the resolving group had problems in language and cognitive skills only prior to school entry. In the late-emerging group, children showed clearly compromised rapid naming. Additionally, their parents had the most severe difficulties in rapid naming, a finding that suggests strong genetic liability. The findings show instability in the diagnosis of dyslexia. The members of the late-emerging group did not have a distinct early cognitive profile, so late-emerging dyslexia appears difficult to predict. Indeed, these children are at risk of not being identified and not receiving required support. This study suggests the need for continued monitoring of children’s progress in literacy after the early school years.