News

Octopus Deploy and Datadog Team Up to Make Software Deployments Less of a Nightmare

• By John K. Waters
• July 14, 2025

Software deployment has always been one of the most stressful parts of a developer's job. You write code, test it, and then push it live, hoping nothing breaks. When something inevitably does go wrong, figuring out what happened can feel like detective work with incomplete clues scattered across different tools and dashboards.

Octopus Deploy and Datadog are trying to solve this problem with a new integration that combines deployment monitoring with broader system observability. The partnership, announced June 9th, connects Octopus Deploy's continuous delivery platform with Datadog's monitoring and security platform to give development teams a unified view of their entire software pipeline.

CI/CD—continuous integration and continuous deployment—is the modern software development practice where code changes are automatically tested, integrated, and deployed to production environments. Instead of releasing software in big, risky batches every few months, teams can push updates multiple times a day. It's faster and more flexible, but it also means there are more moving parts that can break.

When something goes wrong in a CI/CD pipeline, the traditional approach involves jumping between different tools: checking deployment logs in one system, monitoring application performance in another, and correlating infrastructure metrics in a third. It's like trying to solve a puzzle where the pieces are scattered across different rooms.

"To quickly troubleshoot issues with software releases, engineering teams need granular, real-time visibility into their deployment pipelines in the same place they monitor the health and performance of their production services," explained Jimmy Caputo, Director of Product Management at Datadog, in a statement. "By bringing deployment metrics and logs into Datadog, teams can quickly detect failed releases, understand their root causes, and correlate them with broader system performance."

The Octopus-Datadog integration pulls deployment data from Octopus into Datadog's monitoring platform through the Datadog Agent. This means teams can see deployment metrics like average deployment time per environment and deployment failure rates alongside their application performance data and infrastructure monitoring.

The integration captures three types of data from Octopus deployments: performance metrics for tracking things like deployment speed and failure rates, deployment logs for debugging failed releases, and server logs that provide diagnostic information about the Octopus server itself.

For site reliability engineers and operations teams, this creates what the companies call a "single pane of glass" for monitoring. Instead of switching between tools to understand whether a performance issue is related to a recent deployment or an infrastructure problem, they can see everything in Datadog's interface.

"We want to help our customers get working software into production as soon as possible, and the Octopus Datadog integration helps do just that," said Colin Bowern, SVP of Product at Octopus Deploy, in a statement. "Octopus already provides great visibility across your Continuous Delivery pipeline, but with the Octopus Datadog integration, you can see your entire DevOps stack in one spot and correlate data more easily, using two best-of-breed platforms."

This builds on Octopus Deploy's existing monitoring capabilities, which the company has been strengthening throughout 2025. Earlier this year, Octopus added Kubernetes Live Object Status, which provides real-time updates about applications running on Kubernetes clusters. The platform also offers dashboards that show the stage, environment, and state of deployments across multiple repositories.

The integration reflects a broader trend in software development toward observability, the practice of making systems more transparent and easier to understand. As applications become more complex and distributed across cloud services, traditional monitoring approaches that focus on individual components become less effective.

Modern applications might involve dozens of microservices, multiple databases, and various third-party APIs. When something goes wrong, the problem might not be in your code but in how it interacts with these other systems. Having deployment data in the same place as infrastructure and application monitoring makes it easier to spot these connections.

The partnership also highlights how specialized software tools are increasingly working together rather than trying to do everything themselves. Octopus Deploy focuses on continuous delivery, while Datadog specializes in monitoring and observability. By integrating, both companies can focus on their strengths while providing customers with a more complete solution.

The integration is available now and can be configured using instructions in the Datadog Docs. For teams already using both platforms, it's designed to be a straightforward setup process that doesn't require significant changes to existing workflows.

Although the integration won't eliminate all the complexity of modern software deployment, it represents a step toward making one of the most stressful parts of software development a bit more manageable. In a world where applications are expected to work perfectly all the time, having better visibility into what's happening behind the scenes is increasingly essential.