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

[dkpatel patel]

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.

[Staffan Redelius]

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.

1. 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)
2. Verify third-party app functionality. Third party apps many times work differently in cloud compared to On-prem due to differences in the architecture. 
3. 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.
4. 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.
5. 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