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Azure DevOps Server to Services: what really moves (and what doesn’t)

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 In the last few months, I looked more closely at a topic many teams put off: moving from Azure DevOps Server (on‑prem) to Azure DevOps Services (cloud). On paper, it sounds simple – “lift and shift” – but in practice, it is a mix of automated migration and human coordination.

What can be migrated? The good news is that the core platform data usually moves well when you use Microsoft’s Azure DevOps Data Migration Tool (DMT). You can bring across projects and collection configuration, Git repositories with full commit history, and Azure Boards data, such as work items, links, and attachments. Pipeline definitions (YAML and Classic) are migrated as definitions so that teams can see their pipelines in the cloud on Day 1.
What cannot be migrated is important for defining expectations. Pipeline execution history (old runs, logs, artefacts) does not transfer to the cloud. Secrets are another big one: secret variables, tokens and passwords from variable groups or service connections are not exportable by design, so they must be recreated in the target (often from a Vault/Key Vault). Marketplace extensions are not “moved”; you reinstall and reconfigure them. Service connections need re‑authorisation and, in some cases, new login details. And agents are not migrated: if you use self‑hosted agents, they must be re-registered and connectivity verified.
Because of these limits, I see migration as two tracks: (1) migrate what the tool supports, and (2) prepare and rewire the operational dependencies around it. This is why scope boundaries matter a lot, especially in fixed‑price engagements. In the dry‑run, it helps to pick a representative sample of projects and do simple checks: clone/pull repos, open boards, and run a smoke test on a few pipelines (when prerequisites are ready). Another mitigation is to keep the on‑prem Azure DevOps Server in read‑only mode for an agreed retention period, so teams can still check pipeline history.


Team-wise, you don’t need a big army, but you need the right people. A strong setup is one senior infrastructure engineer to lead the migration who is comfortable with DMT validate/prepare, and understands Entra ID group mapping and Azure DevOps permissions. A small “iDevOps buffer” (a few days from an Azure DevOps specialist) can save time. A part-time PM or delivery manager helps to manage the checklist, approvals, and the cutover window.
One risk that is often underestimated: server version. Even if your Azure DevOps Server is “supported”, being behind on updates can create a hidden prerequisite. The migration tooling is version‑specific, and using the wrong build can cause validation to fail. Older patch levels can also bring bugs already fixed in newer releases. If you can, upgrade to the latest supported baseline and patch level before the dry‑run. If you can’t, plan it as a contingency.
Effort depends on scale and complexity, but as an order of magnitude, I often see 5–6 weeks end‑to‑end, including one dry‑run, one production cutover (often weekend), and a few days of hypercare. The biggest drivers are the number of collections, RBAC group complexity, and the number of pipelines that depend on external systems.
The migration tool is powerful, but it is not magic. Success comes from clear scope boundaries, a dry run, and assuring identity, secrets, agents, and connections are ready before you press the cutover button.

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