Abstract: Existence of spam URLs over emails and Online Social Media (OSM) has become a growing phenomenon. To counter the dissemination issues associated with long complex URLs in emails and character limit imposed on various OSM (like Twitter), the concept of URL shortening gained a lot of traction. URL shorteners take as input a long URL and give a short URL with the same landing page in return. With its immense popularity over time, it has become a prime target for the attackers giving them an advantage to conceal malicious content. Bitly, a leading service in this domain is being exploited heavily to carry out phishing attacks, work from home scams, pornographic content propagation, etc. This imposes additional performance pressure on Bitly and other URL shorteners to be able to detect and take a timely action against the illegitimate content. In this study, we analyzed a dataset marked as suspicious by Bitly in the month of October 2013 to highlight some ground issues in their spam detection mechanism. In addition, we identified some short URL based features and coupled them with two domain speciﬁc features to classify a Bitly URL as malicious / benign and achieved a maximum accuracy of 86.41%. To the best our knowledge, this is the ﬁrst large scale study to highlight the issues with Bitly’s spam detection policies and proposing a suitable countermeasure.