Octopus Deploy, a versatile application deployment tool, addresses the challenge of handling rollbacks when deployments fail by allowing users to easily revert to previous successful releases or deploy new ones after fixing issues. The tool does not enforce restrictions on the types of software it can deploy, which means that successful rollbacks require careful system design, especially concerning persistent storage like databases, where schema changes can complicate rollbacks. To support rollbacks, applications should be designed with backward compatibility in mind, and techniques such as Event Sourcing can help ensure that both old and new versions of code can function correctly. Although Octopus provides APIs and features to facilitate deployment recovery, it emphasizes that the overall system design and infrastructure, rather than the deployment tool alone, dictate the ability to automatically recover from deployment failures. The tool offers guidance and support for creating recovery strategies, including suggestions like using a DeployFailed.ps1 script to address specific deployment failures.