This paper investigates the association between private firms’ timeliness of financial reporting and financial health by exploring firms’ reporting behaviour over a longer period of time (9 years). We show that 9% of all firms are consistently late every year and find significant differences in the association between firms’ financial health and late filing depending on their past filing behaviour. We find a negative association between firms’ financial health and late filing. However, our research also shows the opposite (i.e., positive) association for firms who were late consistently. Our results suggest that other motivations besides obfuscating bad performance might cause firms to delay the disclosure of their financial statements.