This article examines the effect of phonological context (singleton vs. clustered consonants) on full phoneme segmentation in Hebrew first language (L1) and in English second language (L2) among typically reading adults (TR) and adults with reading disability (RD) (n = 30 per group), using quantitative analysis and a fine-grained analysis of errors. In line with earlier findings, overall mean scores revealed significant differences between the two groups. However, no qualitative differences were found. In both groups and languages, full phoneme segmentation overall scores for CVC stimuli were higher than CCVC stimuli. This finding does not align with previous findings, obtained from a phoneme isolation task, showing that isolation from a cohesive CV unit is the most difficult. A fine-grained analysis of errors was conducted to glean insight into this finding. The analysis revealed a preference for creating and preserving CV units in phoneme segmentation in both L1 and L2. This is argued to support the cohesion of the CV unit. The article argues that the effect of language-specific sub-syllabic representations on phonemic analysis may not be always observed in overall scores, yet it is reflected in specific patterns of phonological segmentation errors.