Acquiring L2 segments is particularly challenging for L2 learners, especially when the L1 and L2 inventories involve different contrasts and acoustic cues. The present research investigated the perception and production of L2 English vowels by adult Greek-Cypriot learners and examined the effects of orthographic cues and consonantal context in their performance. Perceptual performance was assessed through a forced-choice identification task and production performance through a wordlist-reading and an elicitation task, both analyzed acoustically and through intelligibility ratings. The findings showed the influence of the L1 on both the perception and production of L2 segments, supporting the assumptions of current models of speech perception and production. Learners faced challenges in perceiving the members of L2 contrasts and mostly used their L1 articulatory routines in their productions of L2 vowels. Orthographic cues or consonantal context did not significantly affect learners’ productions or overall perception, although strong contextual effects were observed in individual target vowels. This study is the first to provide an in-depth comparison of CYG and English vowels as well as an examination of the acquisition of L2 English vowels by this population, which can guide EFL teachers and course developers in developing appropriate EFL curricula that incorporate pronunciation instruction.