Enterprise Jira Cloud Adoption Made Easy: Step-by-step Migration Checklist

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The digital landscape is constantly shifting, and so are the needs of modern teams. With cloud adoption becoming a strategic imperative rather than simply a matter of preference, companies across the board are compelled to reinvent their digital core.  

This is where Jira Cloud – Atlassian’s cloud-based project management software – comes into play. The Cloud offers always-on access continuous updates, unparalleled scalability, and robust security – fueling your efforts for high-impact work.  

However, as exciting as Cloud’s possibilities may sound, the success of the project depends on a lot of critical touchpoints. 

Read ahead to learn about the crucial steps which can make your Jira Cloud adoption a success.  

Why move to Jira Cloud? 
 
Impact for organizations who made the shift: 

• Developer productivity increased up to 20% 
• Return on Investment (ROI): 358% 

(Source: Forrester Spotlight: The Total Economic Impact of Cloud Migrations) 

 
Full-proof compliance  
Stringent regulations like GDPR and CCPA add compliance burdens. Jira Cloud offers built-in compliance features and certifications, reducing the need for additional legal expertise and streamlining your compliance journey. Cloud also offers in-built reporting to document compliance efforts and has audit-ready reports in place. 
 
This way, you can eliminate the need for complex on-premises infrastructure and its associated security measures.   
 

Better cross-team collaboration and unlimited storage 
On-premise solutions often have user capacity and data storage limitations which can obstruct collaboration and scalability.  

 
Jira Cloud Standard can support up to 50,000 users. This includes 10,000 users for Jira Work Management, 20,000 users for Jira Service Management, and unlimited users for Jira Software. 
 
If you opt for Jira Premium, you get unlimited storage and advanced roadmaps to track multiple projects across different teams with ease.  
 
The Enterprise plan gets you everything from the Premium plan, plus you can give users access to multiple Jira Software Enterprise products (up to 150) and only pay for each user once. 

 
Innovation-ready ecosystem  
Gartner predicts that by 2025, 95% of new digital workloads will be cloud-native.  

Staying on-premises can mean missing out on cutting-edge features and integrations like AI-powered insights and automation.  

Jira Cloud offers regular feature releases and integrations, ensuring your team always has access to the latest innovations to optimize workflows and adapt to changing needs. 

Getting started with Jira Cloud  

Assessing your readiness 
Before getting started, consider the potential risks associated with the migration, and have a plan for mitigating them. 
 

Make sure to ask yourself the following questions before you get started with your Cloud adoption journey: 
 
Downtime and Business Continuity: 

• What is the expected downtime during the migration, and how will it impact business operations? 
• Is there a business continuity plan in place to address potential issues during and after the migration? 
• Will users be able to access both source and target systems until the migration is completed and sync the changes from target to source (reverse synchronization)? 

Security and Compliance: 

• What security measures and compliance standards does Jira Cloud adhere to? 
• How will sensitive app data be handled in the cloud environment, and what are the data residency and privacy considerations? 

User Training and Change Management: 

• What is the plan for user training to adapt to the differences between Jira Server and Jira Cloud interfaces? 
• How will the enterprise manage the change and ensure a smooth transition for users? 
• Should the migration fail or interrupt at any point, what is the recovery or rollback mechanism? 

Integration with Other Systems: 

• How will the move impact integrations with other tools and systems currently connected to your on-prem tool? 
• Are the integrations compatible with Jira Cloud, and what adjustments are needed? 

Preparing to move to Jira Cloud 
 
Preparing your environment -  

1. Jira, Confluence, Bitbucket Users: 

• Download Final Backups: Before embarking on the migration, ensure you have comprehensive backups of your server and data. 
• Review User Permissions: Examine user permissions and group configurations. Prepare to map these to corresponding roles and access levels in Jira Cloud. 
• Clean Up Data: Identify and archive inactive projects, deleted issues, and unnecessary attachments to optimize data size and expedite migration. 

1. Users of Other On-Premise Tools: 

• Data Compatibility Assessment: Evaluate the compatibility of your current tool’s data format with Jira Cloud’s import mechanisms. Plan for export, transformation, and validation if necessary. 
• Integration Inventory: Create an inventory of existing integrations with your current tool. Identify cloud-based alternatives or API-based connections for each integration. 
• User Training Plan: Develop a management plan for migrating users that addresses the differences between your current tool and Jira Cloud based on roles and responsibilities. 
• Pricing: Determine which Cloud plan is best suited for your team and needs.  

Choosing your migration approach 

Select the most suitable migration approach based on your project complexity and team expertise: 

• Jira Cloud Migration Assistant:  Jira Cloud Migration Assistant (JCMA) is a utility offered by Atlassian to facilitate data and project migration from Jira, Jira Service Management and Jira Core to Jira Cloud. You can install the app from the Atlassian Marketplace.  
  There are Cloud Migration Assistants available for Confluence and Bitbucket as well. 
   
• Manual Migration (CSV Export-Import): Only recommended for highly experienced teams with small, simple instances. It can be risky and requires extensive migration planning due to potential data loss and compatibility issues. 
   
• Third-party Migration Tools: If your organization has a large number of issues and projects or heavily customizes their Atlassian instances - third-party tools often provide robust options for migrating custom fields, workflows, and integrations, reducing the need for manual post-migration configuration. Migrating from a mix of on-premises and cloud deployments (hybrid environments) or from non-Atlassian source systems can be streamlined with advanced mapping and transformation capabilities offered by these tools. There are also zero-downtime 3rd party migration options available, if downtime is a concern. 

Run a test migration 

Sign up for your free cloud migration trial and consider upgrading to a plan with a sandbox environment for safe testing before going live. Install and test the apps you'll use in the cloud, ensuring everyone involved signs off on functionality. 
Successful test migrations build confidence in your cloud migration process. Refine and repeat until everything functions flawlessly for a smooth transition. 

 
 
Post-migration analysis and measuring success 

• Monitor Performance: To ensure a stable migration experience, proactively track user activity, system performance, and error logs in Jira Cloud. 
• Optimize Workflows & Access: Review and optimize workflows and user access controls to ensure they align with your current needs and security best practices. 
• Maintain Security: Continue security best practices by implementing two-factor authentication, enforcing strong passwords, and regularly reviewing user permissions. 
• Seek Feedback & Refine: Gather feedback from users and stakeholders to identify areas for improvement and refine your user management processes for future migrations or updates. 

Conclusion 

By carefully considering your migration approach, leveraging Atlassian's built-in tools, and zeroing downtime, you can ensure a seamless transition to Jira Cloud. This empowers your teams with enhanced collaboration, scalability, and access to the latest Atlassian features, all while laying the foundation for future innovation and growth.