Background: The SARS-CoV-2 pandemic still represents a public health emergency that affects workplaces and forces employers to develop technical, organizational and procedural measures safeguarding workers’ health, particularly ‘fragile’ ones. This research aimed to assess employers’ adherence to the emergency measures planned by the Italian government to hinder COVID-19 during Autumn 2022. Methods: A cross-sectional study was conducted in Autumn 2022, with an 18-item questionnaire derived from the Italian State’s governmental indications, sent by email to 51 companies of Marsica and Peligna Valley, L’Aquila, Southern Italy. Results: A total of 20 recruited companies (65% were micro-enterprises, belonging to the food and financial sector) responded to the questionnaire within a mean time of 18 days (±11.64), which was lower for medium- and large-sized companies as well as for banking sector ones (p < 0.05). As regards intervention strategies, sanitization (92.7% of positive answers) and specific training (83.3%) showed almost full compliance in contrast to working organization (47.5%) and social distancing (61.7%). The companies that reported managing fragility (50%) belong almost exclusively to the banking sector, with predominantly office-based tasks. Conclusions: The study provided insight into critical issues relating to compliance with national legislative directives and the crucial role of occupational physicians as global advisors for all workplaces.