Law firms are slowly but steadily moving to the cloud. According to an American Bar Association report, 37.5% of lawyers reported the use of web-based software services or solutions in 2016, up from 31% in 2015, and 30% in 2014. A recent decision from a federal court in Virginia, however, highlights the substantial risks associated with the use of cloud technology. In that case, the court held that an insurance company had waived any claim of privilege with respect to its claims and investigation files, which had been posted to a publicly-accessible, non-password protected cloud account. Moreover, the court held that the privilege had been waived despite the fact that it was the insurer’s investigator, not the insurer, who had decided to use the unsecured account. The case serves as a warning that use of cloud technology demands that attorneys understand this new technology, and how their clients and agents are using it, in order to protect confidential information maintained there.