The Romanized text has become popular with the growth of digital communication platforms, largely due to the familiarity with English keyboards. In Sri Lanka, Romanized Sinhala, commonly referred to as “Singlish” is widely used in digital communications. This paper introduces a novel context-aware back-transliteration system designed to address the ad-hoc typing patterns and lexical ambiguity inherent in Singlish. The proposed system com bines dictionary-based mapping for Singlish words, a rule-based transliteration for out of-vocabulary words and a BERT-based language model for addressing lexical ambiguities. Evaluation results demonstrate the robustness of the proposed approach, achieving high BLEU scores along with low Word Error Rate (WER) and Character Error Rate (CER) across test datasets. This study provides an effective solution for Romanized Sinhala back-transliteration and establishes the foundation for improving NLP tools for similar low-resourced languages.