Abstract:Singlish, or Colloquial Singapore English, is a language formed from oral and social communication within multicultural Singapore. In this work, we work on a fundamental Natural Language Processing (NLP) task: Parts-Of-Speech (POS) tagging of Singlish sentences. For our analysis, we build a parallel Singlish dataset containing direct English translations and POS tags, with translation and POS annotation done by native Singlish speakers. Our experiments show that automatic transition- and transformer- based taggers perform with only $\sim 80\%$ accuracy when evaluated against human-annotated POS labels, suggesting that there is indeed room for improvement on computation analysis of the language. We provide an exposition of challenges in Singlish annotation: its inconsistencies in form and semantics, the highly context-dependent particles of the language, its structural unique expressions, and the variation of the language on different mediums. Our task definition, resultant labels and results reflects the challenges in analysing colloquial languages formulated from a variety of dialects, and paves the way for future studies beyond POS tagging.