Case Study: Jira Server to Jira Cloud Migration

Since Atlassian’s announcement regarding the discontinuation of Jira Server development,
quite a few companies are moving to Jira Cloud or Jira Data Center (or leaving for alternative products).

We have carried out quite a few such upgrades and migrations for our customers,
and recently we decided to share here the challenges we faced along the way, the conclusions, and the things we learned,
so that you can use this for a similar move you perform alone or with the assistance of a company specializing in the subject.

Challenges along the way:

1. Is Jira Cloud the right fit? We had to evaluate if Jira Cloud was truly the best tool for our needs and if a multi-tenant architecture was the right solution for us.
2. Control and Privacy: Moving to the cloud often means weighing the trade-off of potentially losing some granular control and data privacy.
3. Data Migration: Handling the actual transfer of data is a major undertaking.
4. Workflow Compatibility: We needed to verify if our existing flows and processes would be supported in the new environment.
5. The Marketplace Ecosystem: Not all Jira plugins are created equal. Some are supported in the cloud, while others aren’t; this requires a deep-dive audit.
6. Migration Strategy: There are several ways to migrate. The challenge lies in choosing the path that best aligns with our goals.
7. Integrations: Will everything still talk to each other? We had to ensure continuity for SSO, LDAP, git (GitLab/GitHub), APIs, and webhooks.
8. External Attachments: Managing the transition of external files and data.
9. Feature Parity: Identifying potential loss of functionality, unsupported features, or significant changes in how features behave.
10. The Upgrade Prerequisite: If your Jira Server version is too old, you have to upgrade it first—this is a mandatory step before the move to Cloud can even begin.
11. Timing the Downtime: Selecting the right window for downtime (and preparing for the possibility of more than one).

Note: The challenges are written here in brief. A full breakdown of the challenges can be obtained from us – send us an email at jira@almtoolbox.com.

Key Takeaways and Best Practices for a Smooth Migration

Successfully moving to the cloud isn’t just a technical task; it’s a strategic transition. Based on our experience, here are the essential best practices for ensuring your migration is a success:

1. Treat it as a Formal Project: Migration is not a “side task” to be handled whenever there’s free time. It requires dedicated focus, strategic thinking, and buy-in from multiple stakeholders across the organization.
2. Build a Robust Roadmap: Start by mapping out your work plan. Identify potential risks and their implications early to develop mitigation strategies. Ensure you map every plugin and define every step of the migration sequence.
3. Execute a “Dry Run” in Jira Cloud: Set up a Jira Cloud test environment to perform a trial migration. While free instances are available for testing, there is a specific methodology required to do this correctly without compromising your data. (For more details on the right way to set this up, contact us below).
4. Designate a Project Owner: Success requires a dedicated lead on the client side. Without internal commitment and clear accountability, the project can easily lose momentum.
5. Test, Test, and Test Again: Thorough validation is the only way to prevent post-migration downtime.
6. Patience and Expertise are Key: This process requires specialized knowledge and realistic timelines. Depending on the complexity, a full migration can span several months from start to finish.
7. Know When to Call the Experts: Many companies outsource this process to specialized partners (like us) to ensure a seamless transition. While smaller teams with simple, “vanilla” setups and few users may manage it solo, complex environments usually require professional intervention.
8. While Atlassian offers free migration tools, our experience shows they have significant limitations:
   • Scalability Issues: They generally only perform reliably for small organizations of 10–20 people.
   • The “Vanilla” Constraint: These tools are designed for “out-of-the-box” environments. If you have customized your configurations, added unique “stitching,” or integrated third-party plugins, the free tools will likely fail.
   • Complex Environments: In any sophisticated or highly customized environment, standard migration scripts often crash or result in data loss.

Note: The conclusions are written here in brief. A full breakdown of the challenges and conclusions can be obtained from us – send us an email at jira@almtoolbox.com.

Relevant links:

• Our Jira website
• Projects we executed around JIRA
• Case Study: Moving from Jira Cloud to Jira Data Center

This article was originally published in February 2022 and has been updated several times since.