Since the times of the old Arab grammarians, the syllable has played a major role in the phonology of classical as well as colloquial Arabic. In the 1970s, phonologists investigated Cairene Arabic (CA) syllable structure and found it to be the domain of some phonological processes, such as emphatic spread, CVC syllables light word final but heavy word internally, limitations on consonant clusters in certain positions of a word, and epenthesis of a vowel to break consonant clusters if there happen to be more than two consonants in word concatenation. This paper discusses some CA phonological phenomena investigated through different theories in generative phonology, i.e. rule based, autosegmental and Optimality Theory (OT). An overview of early theories is given. Early generative theories contributed substantially to the theory of the syllable of CA; however, each theory was able to explain a given phonological phenomenon. It is through the generative Optimality Theoretic approach that more than one phenomenon can be described and analyzed. The paper’s aim is not to compare between the different theories, but to describe the progression CA syllable structure analysis took in generative phonology. Unlike earlier research which based conclusions on some CA words mixed with some other classical Arabic words pronounced by CA native speakers, this paper presents an Optimality Theoretic analysis that is based on uniquely CA phonetic outputs. The analysis finds that some syllable structure constraints are high ranked and inviolable such as ONSET, and *[μ μ μ]σ. The study also shows that OT analysis can illustrate and explain in one representation, i.e. tableau two different phonological phenomena, insertion and deletion of a vowel in consonant clusters, despite their relatedness to separate prosodic domains, the syllable, the prosodic word, and the phrase. This is carried out by analyzing the ranking, relationship and interaction between the following constraints, ONSET MAX-IO, *[μ μ μ], *COMPLEX CODA, DEP-IO >> NOCODA, *APPENDIX; -*V,+hi]$:, ALIGNR (σ, PrWd), and LINEARITY. The study analyzes data that is mainly from Cairene spoken Arabic, attempting to fill a gap created by one of the contentious issues related to studies of the phonology of CA, and that is mixing between colloquial Cairene and classical Arabic.