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