Penetration Testing and Red Team attack simulations performed against internal networks or applications require a reliable connection to that environment. While this connection is often achieved via software agents, virtual machines, or on-site penetration testers, the use of a purpose built "dropbox" computer for remote access is a preferred method for many engagements.

In building out these testing platforms, the testing goals we are looking to achieve help us define the dropbox we assemble. A covert Red Team challenging defender's skills in detection, discovery, and attribution will require a very different build than a system supporting concurrent penetration testers and vulnerability scanning. We will cover the myriad of hardware, software, power, and communication decisions to work through and infrastructure needed to support those choices.

Although specific hardware and software options will be mentioned, this presentation focuses on helping us make the best decisions from the available choices rather than providing detailed but instantly out-of-date build instructions.

We will wrap things up by discussing some of the dropbox systems penetration testers and threat actors have been using in the field and cover a few legal considerations that will help keep you on the right side of the law.