In a special double-episode of "Will it Deploy?", Rob Pearson explores the automation of deploying a multi-tenant SaaS web application to various customers using Octopus Deploy and AWS virtual machines. The featured application, Random Quotes, is a Microsoft ASP.NET Core 2.0 web app utilizing Entity Framework Core 2.0 and Microsoft SQL Server 2017, designed to demonstrate the complexities of multi-tenant deployments with features like customized settings and dynamic module loading. The deployment process involves several steps using Octopus Deploy, such as copying database scripts, executing migration scripts, and deploying specific modules based on customer subscriptions, all detailed in the episode's GitHub repository. Pearson invites viewers to suggest future topics and encourages subscriptions to their YouTube channel for more content.