URL shortening services have become extremely popular. However, it is still unclear whether they are an effective and reliable tool that can be leveraged to hide malicious URLs, and to what extent these abuses can impact the end users. With these questions in mind, we first analyzed existing countermeasures adopted by popular shortening services. Surprisingly, we found such countermeasures to be ineffective and trivial to bypass. This first measurement motivated us to proceed further with a large-scale collection of the HTTP interactions that originate when web users access live pages that contain short URLs. To this end, we monitored 622 distinct URL shortening services between March 2010 and April 2012, and collected 24,953,881 distinct short URLs. With this large dataset, we studied the abuse of short URLs. Despite short URLs are a significant, new security risk, in accordance with the reports resulting from the observation of the overall phishing and spamming activity, we found that only a relatively small fraction of users ever encountered malicious short URLs. Interestingly, during the second year of measurement, we noticed an increased percentage of short URLs being abused for drive-by download campaigns and a decreased percentage of short URLs being abused for spam campaigns. In addition to these security-related findings, our unique monitoring infrastructure and large dataset allowed us to complement previous research on short URLs and analyze these web services from the user’s perspective.