Portscout is a tool which looks for new versions of software in the FreeBSD ports tree, and potentially other software repositories. It is also possible to provide an arbitrary list of software in a simple XML format. Various factors make this task a bit more difficult than it might initially seem. In particular, the array of weird and wonderful versioning schemes software vendors manage to come up with. Portscout spawns several child processes and does its version checking in parallel, while attempting to best-guess strange-looking version numbers, navigate around unhelpful sites and web servers, and contend with the CPU-heavy rapidly-expanding FreeBSD ports system. In addition to all this, it is possible to generate nice HTML reports and send reminder mails to interested parties.