Variability in the form of article (i.e., a and the) omissions and stressing has been attributed to a mismatch between first (L1) and second language (L2) prosodic and syntactic structures. An overlap between the L1 and L2 systems, on the other hand, is expected to contribute to native-like article productions. This case study aims to explore the role of L1 prosodic structure (Turkish, Spanish and English) and syntactic environment (nouns with and without adjectives) on article productions of two end-state L2 speakers and one Australian-English native speaker. The data consisted of a sentence imitation task and spontaneous speech recordings of these three speakers. Article use patterns in the data were coded as supplied and omitted, and indefinite article durations were excised and measured using PRAAT. The findings suggest that the presence of an adjective in the noun clause increases cognitive demand, since irrespective of the L1 background, all the speakers had longer indefinite article durations in contexts with an adjective. Second, the Turkish speaker, whose L1 has a different prosodic and syntactic structure from Spanish and English for encoding definiteness, had higher rates of article stressing and omissions in contexts with an adjective. Third, L1 prosodic constraints can be responsible for article stressing and omissions in end-state L2 speech since only the prosodic transfer hypothesis predicts a difference in article durations between the two syntactic environments within the interlanguage of the same speaker. Despite long years of exposure to and frequent daily use of the L2, the persistent difficulty in article productions, as reported in this paper, may imply the importance of age of acquisition in overriding certain L1 prosodic effects in acquiring an L2.