Ever had your site go down because Jim accidentally copied over the web.config? Ever broken out into a cold sweat because you forgot the where clause was in a production update script? Well stop deploying like an idiot. Deploying applications has traditionally been one of the most dangerous parts of software development. It's often very hands-on, relying on the right people doing the right thing at the right time, and is therefore extremely prone to failure. In this presentation, I'll briefly look at why developers should automate their deployment process as soon as possible. I'll looks at some of the ways teams try to manage their deployments and reduce the danger. Finally, I'll show you why a tool like Octopus Deploy is the best way to do it. We'll look at some real-world Octopus implementations, including very complex environments, in-depth testing, and automated rollbacks.