Morphological processing of derived words develops simultaneously with reading acquisition. However, the reader’s engagement in morphological segmentation may depend on the language morphological richness and orthographic transparency, and the readers’ reading skills. The current study tested the common idea that morphological segmentation is enhanced in non-transparent orthographies to compensate for the absence of phonological information. Hebrew’s rich morphology and the dual version of the Hebrew script (with and without diacritic marks) provides an opportunity to study the interaction of orthographic transparency and morphological segmentation on the development of reading skills in a within-language design. Hebrew speaking 2nd (N = 27) and 5th (N = 29) grade children read aloud 96 noun words. Half of the words were simple mono-morphemic words and half were bi-morphemic derivations composed of a productive root and a morphemic pattern. In each list half of the words were presented in the transparent version of the script (with diacritic marks), and half in the non-transparent version (without diacritic marks). Our results show that in both groups, derived bi-morphemic words were identified more accurately than mono-morphemic words, but only for the transparent, pointed, script. For the un-pointed script the reverse was found, namely, that bi-morphemic words were read less accurately than mono-morphemic words, especially in second grade. Second grade children also read mono-morphemic words faster than bi-morphemic words. Finally, correlations with a standardized measure of morphological awareness were found only for second grade children, and only in bi-morphemic words. These results, showing greater morphological effects in second grade compared to fifth grade children suggest that for children raised in a language with a rich morphology, common and easily segmented morphemic units may be more beneficial for younger compared to older readers. Moreover, in contrast to the common hypothesis, our results show that morphemic segmentation does not compensate for the missing phonological information in a non-transparent orthography, but rather that morphological segmentation is most beneficial in the highly transparent script. These results are consistent with the idea that morphological and phonological segmentation processes occur simultaneously and do not constitute alternative pathways to visual word recognition.