Migrating from PagerDuty to Datadog On-Call can quickly become complicated when dealing with multiple teams, schedules, and escalation policies. Datadog built an import workflow that provides a step-by-step, self-service way to migrate team configurations, but requires that you already have the PagerDuty integration installed and requires the running user to have user invitation permissions, which can be of limited use with external provisioning.

RapDev has developed an automated, API-driven framework designed to streamline this process, understand your cutover holistically, and ensure that on-call structures are rebuilt accurately and consistently in Datadog.

How the process works

Our framework focuses on visibility, validation, and automation. Before any data is created in Datadog, the system runs a full export from PagerDuty and generates a comprehensive pre-migration report. This report shows exactly how teams, schedules, and escalation policies will map into Datadog, enabling review and adjustment before any changes occur.

The typical workflow includes:

1. Pre-migration analysis: Extract team, user, and schedule data from PagerDuty using its API.
2. Pre-migration report: Generate a detailed mapping document showing how each entity aligns with Datadog’s On-Call model, including routing and escalation relationships.
3. Bulk import: Once validated, the data is pushed into Datadog using the On-Call API, creating teams, schedules, and policies in a single automated pass.
4. Post-migration sync: Use the newly established team relationships in Datadog to update monitors that previously referenced PagerDuty notification handles, ensuring alerts continue routing properly.

Why this approach matters

This process eliminates the manual rebuilds typical of point-and-click migrations, providing:

• Consistent data mapping across all teams and schedules.
• A repeatable, auditable process that supports organizational standards.
• The ability to identify and correct inconsistencies before committing changes.
• A foundation for future automation, including Terraform-based On-Call management.

By combining automation with upfront validation, RapDev’s approach allows engineering teams to move into Datadog On-Call faster, with full confidence in the integrity of their on-call workflows.

If you're ready to streamline your On-Call migration, reach out to us.