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Twitter has emerged as one of the most popular platforms to get updates on entertainment and current events. However, due to its 280-character restriction and automatic shortening of URLs, it is continuously targeted by cybercriminals to carry out drive-by download attacks, where a user’s system is infected by merely visiting a Web page. Popular events that attract a large number of users are used by cybercriminals to infect and propagate malware by using popular hashtags and creating misleading tweets to lure users to malicious Web pages. A drive-by download attack is carried out by obfuscating a malicious URL in an enticing tweet and used as clickbait to lure users to a malicious Web page. In this article, we answer the following two questions: Why are certain malicious tweets retweeted more than others? Do emotions reflecting in a tweet drive virality? We gathered tweets from seven different sporting events …