What is the best way to migrate existing Jira issues from Server to Cloud without losing our custom

[Ali Ali]

Hello Atlassian Community,

We’re currently managing several ongoing food-related projects at MyFoodValley.net, where our team tracks everything from recipe development to marketing campaigns using Jira Server.

Our Jira Server setup has a few custom workflows built around our food content process — for example:

• “Recipe Concept → Ingredient Testing → Review → Published”

• “Product Idea → Supplier Check → QA Approved → Featured”

We’re planning to move to Jira Cloud soon for better collaboration and integration with Confluence Cloud, but we’re concerned about preserving our custom workflow statuses and transitions during migration.

We’ve reviewed some official documentation about the Cloud Migration Assistant, but there’s still some confusion:

1. Will our custom workflow schemes and transitions (e.g., “Ingredient Testing”) migrate automatically, or do we need to recreate them manually on Cloud?

2. How should we handle custom field mappings (like “Cuisine Type” or “Nutritional Tags”) to ensure they don’t break post-migration?

3. Is there a recommended order (projects, workflows, users, fields) for smoother migration, especially for teams managing multiple food-related sub-projects?

4. Has anyone experienced status mismatches or lost transitions after using the migration assistant — and how did you fix them?

5. Are there any best practices for testing the migration with a small sample of issues first?

Our goal is to keep our existing food content workflows intact, since our editorial and kitchen teams depend heavily on these custom statuses to track progress from idea to publication.

Any guidance, documentation links, or real-world tips from teams that have migrated from Server → Cloud while maintaining workflow integrity would be greatly appreciated!

Thanks in advance 🙏
– The MyFoodValley.net DevOps & Content Team

[Gor Greyan]

Hi @Ali Ali

You’re on the right track! Jira Cloud Migration Assistant (JCMA) can move your workflows, fields, and issues — but a few best practices will help you preserve everything cleanly:

1. Custom Workflows & Transitions

   • Native workflows, statuses, and transitions migrate automatically with JCMA.

   • Custom triggers or post-functions from Server-only apps won’t — rebuild those manually in Cloud.

   • Statuses like “Ingredient Testing” or “Supplier Check” will appear fine if part of active workflow schemes.

2. Custom Fields

   • Standard custom fields migrate with values.

   • Plugin-based fields require the same app on Cloud or manual recreation (CSV import if needed).

3. Migration Order

   • Step 1: Inventory & clean up unused workflows/fields.

   • Step 2: Migrate users first.

   • Step 3: Run a test migration (one project).

   • Step 4: Validate results → full migration.

4. Testing & Validation

   • Pick one smaller project for a pilot.

   • Check each status transition, field value, and board post-migration.

   • Fix mismatched fields or automation rules before scaling.

5. Common Pitfalls

   • Missing transitions → rebuild in Cloud.

   • Blank fields → reimport via CSV.

   • User mismatches → ensure identical emails.

   • App data → verify plugin Cloud support early.

You can use the following documentation:

https://support.atlassian.com/migration/docs/cloud-migration-methods-for-jira/
https://support.atlassian.com/migration/docs/what-gets-migrated-with-the-jira-cloud-migration-assistant/
https://community.atlassian.com/forums/Jira-Cloud-Admins-articles/How-to-Build-a-Cloud-Migration-Playbook-for-Jira-and-Confluence/ba-p/3107011

[Ankita Mehta-OpsHub_ Inc]

Hi @Ali Ali

Migrating from Server to Cloud isn’t hard, but keeping your workflow logic intact does need a bit of prep. Since those custom workflows sound like the heart of your process, here are a few things to keep in mind before you begin: 

• Workflows: Most statuses and transitions migrate fine, but anything tied to custom post-functions or validators will need to be recreated in Cloud (as rightly mentioned by Gor in the above response)
• Custom fields: Check that the same fields (like Cuisine Type or Nutritional Tags) exist in Cloud with matching types as mismatches are a common reason for mapping issues. 
  Order of migration: Bring over users and custom fields first, then projects and workflows. That helps avoid unmapped items. 
• Testing: Always do a pilot migration with one project to confirm statuses, transitions, and data fidelity. 
• Validation: After the test, compare a few key workflows side by side between Server and Cloud to make sure everything lines up. 

You may consider OpsHub Migration Manager (OMM), an Atlassian Silver Solution Partner and enterprise - grade data migration platform. OMM supports phased or full migrations with zero downtime, no disruption, and no data loss, and even offers reverse sync back to Server if you want to roll changes during testing. It maintains high data fidelity including attachments, comments, relationships, and field mappings- so your custom recipe and content workflows move to Cloud exactly as they are.

For more information, you may find this Atlassian marketplace listing useful.

Hope it helps :)