Privacy Masking is a critical concept under data privacy involving anonymization and de-anonymization of personally identifiable information (PII). Privacy masking techniques rely on Named Entity Recognition (NER) approaches under NLP support in identifying and classifying named entities in each text. NER approaches, however, have several limitations including (a) content sensitivity including ambiguous, polysemic, context dependent or domain specific content, (b) phrasing variabilities including nicknames and alias, informal expressions, alternative representations, emerging expressions, evolving naming conventions and (c) formats or syntax variations, typos, misspellings. However, there are a couple of PII datasets that have been widely used by researchers and the open-source community to train models on PII detection or masking. These datasets have been used to train models including Piiranha and Starpii, which have been downloaded over 300k and 580k times on HuggingFace. We examine the quality of the PII masking by these models given the limitations of the datasets and of the NER approaches. We curate a dataset of 17K unique, semi-synthetic sentences containing 16 types of PII by compiling information from across multiple jurisdictions including India, U.K and U.S. We generate sentences (using language models) containing these PII at five different NER detection feature dimensions - (1) Basic Entity Recognition, (2) Contextual Entity Disambiguation, (3) NER in Noisy & Real-World Data, (4) Evolving & Novel Entities Detection and (5) Cross-Lingual or multi-lingual NER) and 1 in adversarial context. We present the results and exhibit the privacy exposure caused by such model use (considering the extent of lifetime downloads of these models). We conclude by highlighting the gaps in measuring performance of the models and the need for contextual disclosure in model cards for such models.