A distributed workforce is becoming the trend as new companies start and take off, as well as existing companies expand. Traditional and proven security principles do not always apply to this type of environment, thus requiring unique and creative solutions. One of the challenges with a distributed workforce is the ability to protect end users as they perform day-to-day work and browse the deep wide internet (personal browsing habits). The ability to monitor end users and production systems becomes increasingly difficult as software and hardware are migrated from physical assets and virtualized into the cloud. We have a unique deployment and workforce requiring different approaches to maintain a secure workforce. This talk covers the gaps that exist and approaches we are taking and researching to maintain a safe and secure work environment.