Cloud Migration Roadmap for Moving On-Premise Servers to the Cloud

Question

We are planning a server-to-cloud migration and are looking for a practical, experience-based roadmap to approach it in a structured way.

Our current focus is on:

* Assessing existing on-premise infrastructure and application dependencies

* Sequencing workloads to minimize downtime and operational risk

* Handling data migration and validation

* Post-migration monitoring and optimization

We want to ensure a smooth transition without disrupting live environments or critical workflows.

I’ve come across a few general approaches, but I’m interested in hearing from the community about:

* How you typically define a cloud migration roadmap

* Common challenges you faced during migration

* Best practices or lessons learned that helped avoid issues

For additional context, I’ve reviewed this external reference that outlines a structured cloud migration roadmap, which may help frame the discussion:
🔗 https://www.azilen.com/learning/cloud-migration-roadmap/

Looking forward to insights from those who have handled similar migrations.

Dr_ Ankita Mehta-OpsHub_ Inc · Answer

Hi @dkpatel patel

Welcome to the Atlassian Community,

Cloud migrations can feel overwhelming, especially when production environments are involved. A structured roadmap makes all the difference.

A few key considerations:

Start with dependency mapping-apps, integrations, identity, and data flows.

Prioritize workloads based on business criticality and complexity.

Plan data validation checkpoints, not just final verification.

Define rollback and downtime windows clearly.

Post-migration monitoring should include performance baselining.

In your case, you may want to explore OpsHub Migration Manager (OMM), an Atlassian Solutions Partner. It supports phased or full migrations, ensures no downtime or disruption, and preserves historical fidelity including comments, attachments, and relationships.

You may refer to the following links on the Atlassian Community to get a holistic picture of Jira DC to Jira Cloud migration:

1) Jira Cloud: New Tool Adoption Steps - Atlassian Community

2) The Jira Data Center Migration Blueprint: 10 Best ... - Atlassian Community

3) Which Jira Cloud Migration Approach Is Right for Y... - Atlassian Community

4)  Jira DC to Jira Cloud migration listing on Atlassian marketplace

Have a great day ahead!

Staffan Redelius · Answer

Hi @dkpatel patel and welcome to the Community!

I did a quite large migration from Server to Cloud (Jira and Confluence) a couple of years ago and can give you some advice.

* Clean before you move. Remove unused apps, attachments, projects, custom fields and workflows etc. This will make the migration easier and if you are moving to Cloud Standard you will have limited storage (250 GB/Atlassian app)
* Verify third-party app functionality. Third party apps many times work differently in cloud compared to On-prem due to differences in the architecture. 
* Identify projects/spaces that needs to be migrated toghether. Try to "decouple" dependencies as much as possible. If a migration breaks for some reason you will have to delete the project in the target environment clean-up and redo the migration. If you have a large cluster of projects this will be complicated and time consuming.
* All fields will not be possible to migrate. This might be better nowdays but when I did the migrations you needed to update certain fields via csv.
* Do not change anything in shared schemas for the migrated projects. This might also have changed but earlier any changes in shared schema broke the migration and prevented further migrations.

Confluence is easier to migrate than Jira but point 1 and 2 above still apply.

These are quite general pointers. It might be good to partner up with someone that has done these type of migrations before to get more specific advice.

If you have any additional or more specific questions just add them to this thread so we can help you further.

Best regards,
/Staffan