Octopus Easy Mode - Retries

Matthew Casperson's article, published on February 2, 2026, explores enhancing deployment processes by adding retry logic to steps in Octopus deployments. The guide requires an Octopus Cloud account and the Octopus AI Assistant Chrome extension, emphasizing the simplicity of the cloud-hosted version over on-premises setups. By creating a project titled "04. Script App with Retries," users can enable retries on script steps and simulate failures by having the script randomly fail 50% of the time, thus triggering the retry mechanism. The article notes that while invalid PowerShell scripts may occur due to the AI's output, this still serves the purpose of demonstrating retry logic. The next phase involves incorporating build information into the deployment process, marking an ongoing journey in DevOps automation with AI assistance.

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