The objective of this paper is to find out which factors best explain why SMEs delay their annual reports (DAR). Relying on various theoretical streams, we use three types of variables to explain DAR: past DAR behaviour of managers, corporate governance characteristics and occurrence of financial distress. The study is based on the whole population data from Estonia, with a total 59,294 unique firms. Two types of DAR, i.e., short- and long-term delays, are used as dependent variables in the logistic regression analysis. The paper indicates that both types of today’s DAR are best explained by the previous DAR behaviour of managers, especially in the nearest past. Financial distress has a lower, but still acceptable explanatory power, while it remains weak for the corporate governance characteristics. Firm size and age have an impact on the results. As the paper indicates the prominence of recurrent violation behaviour in explaining DAR, the legal framework and its implementation could be adjusted to take account of this fact. The linkage of DAR and financial distress suggests the inclusion of the former into credit scoring models.