Can a generation that documents and shares more information than ever before truly keep anything secret? Did the advent of Facebook, Dropbox, and Google Docs come at the expense of the last shreds of discretion left in the fingertips of Generation Y? Has the overarching idea of what is “discreet” shifted with the Digital Age and new social norms? And if so, should trade secrecy, a doctrine already shrouded in the constantly changing tides of equity, reflect a new concept of what is reasonable?In the wake of scandalous reports regarding the many indiscretions of spy chief David Patraeus, these seemingly rhetorical questions are more relevant and demanding of answers than ever. Patraeus’ affair with Paula Broadwell surfaced during an FBI investigation of “jealous” e-mails allegedly sent by Broadwell to a woman named Jill Kelley. The New York Times posed the question, “If David H. Patraeus couldn’t keep his affair from prying eyes as director of the Central Intelligence Agency, then how is the average American to keep a secret?” Experts on privacy say people grossly underestimate how transparent their digital communications are, regardless of whether the Federal Bureau of Investigation is looking into their personal lives.Transparency of communication is undoubtedly an issue for businesses as well. “Many IT professionals recognize the benefits cloud computing offers in terms of increased storage, flexibility and cost reduction” said Songnian Zhou, chief executive officer of Platform Computer. The phenomenon of easy information sharing is automatically in tension with the perpetual need for businesses to keep their proprietary information secret. “Considerations such as secrecy, data privacy, network performance, and economics are likely to lead to a mix of cloud computing centers both within the company firewall and outside of it,” said Julian Freidman, a specialist in emerging technologies. Juxtapose that notion with that of New York Times reporter Nicole Pelroth, who wrote, “Face it: no matter what you are trying to hide in your e-mail in-box or text message folder — be it an extramarital affair or company trade secrets — it is possible that someone will find out,” and it is clear that businesses must find some happy medium between the accessibility of their information and how to also keep proprietary information away from prying eyes and inboxes.With the tension between accessibility and secrecy in mind, I will lay out the basic trade secret prima facie cause of action, and then analyze the doctrine through the lens of social media and cloud computing, focusing on whether information shared through social media, or stored on the cloud is reasonably protected. I will argue that the reasonableness standard should be flexibly applied to work with changes in the accessibility of data, and that the flexibility should be reflected in trade secret law. Alternatively, I will explore the ramifications of not applying a flexible reasonableness standard to trade secrecy, and how that could diminish the utility of the doctrine as a whole over time.