This paper documents significant associations between the disclosure ratings by analysts (produced by the Association of Investment Management and Research) and publicly accessible and quantifiable disclosure characteristics. These characteristics include disclosure quantity and disclosure timeliness. Results show that firms with longer Business and MD&A sections in annual reports, and firms that file timely reports, receive higher annual report scores. These results are robust after controlling for factors that may affect unobservable disclosure quality such as firm fundamentals, earnings attributes, and company popularity among analysts. Based on the observed association, this paper further attempts to predict the AIMR ratings using quantifiable disclosure data. At a reasonable accuracy rate, the quantity-based predictions reach conclusions consistent with the AIMR scores. This highlights the plausibility of using quantitative disclosure attributes as an efficient indicator of disclosure quality on a large scale.