What are the biggest challenges you've faced while migrating from Jira Data Center to Jira Cloud?

[jameers]

Hello Atlassian Community,

Many organizations are planning or actively migrating from Jira Data Center to Jira Cloud to take advantage of Atlassian Cloud's scalability, innovation, and reduced infrastructure management.

While every migration is unique, I'm interested in learning from real-world experiences and best practices from this amazing community.

I'd love to hear your thoughts on the following:

- What was the biggest challenge during your migration?
- How did you plan and execute the migration?
- Were there any issues with apps or Marketplace plugins? If so, how did you handle them?
- How did you migrate custom workflows, custom fields, permissions, and automation rules?
- Did you experience any performance or data migration issues?
- How did you manage user communication, training, and change management?
- What security or compliance considerations were most important for your organization?
- If you could restart the migration, what would you do differently?
- What tools, documentation, or migration strategies would you recommend to others?

From my perspective, some of the common challenges include:

- Assessing app compatibility between Data Center and Cloud
- Managing complex workflows and customizations
- Cleaning up unnecessary configurations before migration
- Preserving integrations with tools like GitHub Enterprise, ServiceNow, and identity providers
- Minimizing downtime while ensuring data integrity
- Helping users adapt to the Jira Cloud experience

I'm looking forward to hearing about your experiences, lessons learned, and recommendations. Your insights could help many teams prepare for a smoother migration journey.

Thanks in advance for sharing your expertise!

[Brita Moorus]

Hi, @jameers 👋 Great question.

From my experience, the biggest DC → Cloud migration challenges are usually:

• Apps and Marketplace plugins as not every DC app has a Cloud equivalent, and even when it does, the features sometimes may differ. App assessment should start as early as possible.

• Legacy configuration cleanup - old workflows, custom fields, schemes, inactive projects, old users and groups… 🦖 Migrating everything as-is usually makes Cloud harder to adopt.

• User and group mapping - especially with multiple directories, inactive users, duplicate accounts, or unclear group naming.

• Integrations - SSO, email handlers, REST/API integrations, development tools, BI tools, etc. These often need redesign, not just migration.

• Automation and permissions - most configurations migrate quite well with the migration assistant, but I would still validate workflows, permissions, notifications, boards, filters, dashboards, and automation rules carefully after each migration.

• Change management - Cloud has different admin, UI, security, and app behaviour. Training and communication matter a lot 💙

What I’d recommend:

• run at least one test migration

• clean up as much as possible before migrating

• assess apps early

• freeze major configuration changes before the final migration

• prepare a clear user communication plan

• validate with real project owners, not only admins

A couple of Community articles/discussions that may also be useful reads:

• Top Jira Cloud Migration Challenges and How to Address Them - good overview of practical migration pain points, not just the technical part.

• The Jira Data Center Migration Blueprint: 10 Best Practices for Moving to Jira Cloud - useful checklist-style article for planning, cleanup, stakeholder alignment, and testing.

• How to Build a Cloud Migration Playbook for Jira and Confluence - nice read if you want a more structured migration plan with responsibilities, timelines, and lessons learned.

• Jira Instance Cleanup Guide - not migration-specific only, but very relevant. Cleanup before migration can save a lot of pain later.

Hope these help 💙 Cloud migration is usually 30% tooling and 70% cleanup, preparation, decisions, and communication 😊