The Complete Jira Server to Jira Cloud Migration Playbook: Checklist, Tools, Security & Performance Tips

Estimated Reading Time: 19 minutes

• Introduction
• Understanding the Migration Landscape
• Business Case & Benefits of Cloud
• Pre-Migration Planning & Governance
• Choosing the Right Atlassian Cloud Migration Tools
• Step-by-Step Jira Server to Jira Cloud Migration Procedure
• Step-by-Step Confluence Server to Cloud Migration
• Security & Compliance in Atlassian Cloud
• Post-Migration Performance & Optimization
• Comparative Analysis Recap
• Case Studies & Success Stories
• FAQ
• Conclusion & Next Steps

Introduction

Jira Server to Jira Cloud migration is top-of-mind for thousands of teams today as Atlassian continues to invest heavily in their Cloud offerings while moving away from self-hosted solutions. The significant surge in Atlassian Cloud adoption reflects an industry-wide shift toward software-as-a-service models, making proper Atlassian Data Center migration planning absolutely essential for success. Organizations of all sizes face critical decisions about timing, methods, and strategies to ensure business continuity during this transition.

Whether you’re planning a standalone Jira migration or a more complex Confluence Server to Cloud migration alongside other Atlassian tools, this comprehensive playbook provides the guidance you need. We’ll cover everything from building your migration checklist and selecting appropriate Atlassian Cloud migration tools to addressing Atlassian Cloud security compliance concerns and implementing Atlassian Cloud performance optimization techniques post-migration.

If your organization is planning a broader DevOps transformation alongside your Atlassian migration, it’s highly recommended to follow a dedicated DevOps Migration Planning Guide for risk assessment, downtime strategies, and organizational alignment.

By the end of this guide, you’ll have a clear understanding of the Atlassian Cloud vs Server comparison, enabling you to make informed decisions and execute a seamless migration for your organization.

Understanding the Migration Landscape

Key Migration Scenarios Defined

Jira Server to Jira Cloud migration refers to the process of transferring projects, issues, workflows, and user data from your on-premise Jira Server/Data Center installation to Atlassian’s hosted Cloud environment. This transition shifts responsibility for infrastructure, maintenance, and upgrades from your internal teams to Atlassian.

Confluence Server to Cloud migration involves moving spaces, pages, attachments, macros, and permissions from your self-hosted Confluence Server/Data Center instance to Atlassian’s Cloud platform. This migration requires careful attention to content structure and macro compatibility.

Many organizations operate integrated Atlassian environments, where Jira and Confluence work together along with other tools like Bitbucket or Bamboo. In these cases, migrations often need to happen in parallel or in a carefully sequenced manner to maintain cross-product integrations and references.

If your migration includes version control or cross-platform DevOps elements, such as Bitbucket to GitHub or Azure DevOps, read our Cross-Platform DevOps Migration Guide for workflow preservation and metadata transfer strategies.

Atlassian Cloud vs Server Comparison

When evaluating the move from Server to Cloud, several key differences should inform your decision:

• Upgrade Management: Cloud provides automatic, incremental updates managed by Atlassian versus manual patching and version upgrades for Server/Data Center.
• Cost Structure: Cloud shifts to an OPEX (subscription) model with predictable monthly/annual costs versus the CAPEX (hardware/license) approach of Server with periodic renewal spikes.
• Scalability: Cloud offers built-in scalability that automatically adjusts to your needs versus vertical scaling and clustering requirements in Data Center.
• App Ecosystem: While the Cloud Marketplace is growing rapidly, some app parity gaps still exist compared to Server. Always verify your critical apps are available for Cloud before migrating.
• Customization Options: Cloud has certain limitations on customizations compared to Server, particularly regarding database access, filesystem modifications, and custom code deployments.

For organizations embarking on broader ALM transitions, our Microsoft ALM Integration Strategy offers a detailed comparison of major ALM platforms and considerations for integrating Jira/Confluence into a modern development landscape.

Atlassian maintains a detailed feature parity matrix to help you understand specific functional differences between Server and Cloud versions of their products.
Cloud migration methods for Jira

Business Case & Benefits of Cloud

Moving to Atlassian Cloud delivers several strategic advantages that justify the migration effort:

• Reduced Operational Overhead: By eliminating the need to manage infrastructure, apply upgrades, and maintain servers, IT teams can redirect resources toward higher-value activities. This alone can represent significant cost savings in personnel time and infrastructure expenses.
• Predictable Cost Structure: Cloud subscriptions provide clear visibility into ongoing costs with options for monthly or annual billing, making budgeting more straightforward compared to Server’s upfront licensing and renewal model.
• Accelerated Innovation: Atlassian delivers new features to Cloud first, with continuous updates that don’t require planning maintenance windows or downtime. Teams gain immediate access to enhancements and can benefit from mobile access through dedicated apps.
• Enterprise-Grade Reliability: Atlassian Cloud offers built-in disaster recovery and high availability with documented SLAs ranging from 99.9% to 99.95% uptime, depending on your plan. This level of reliability would require significant investment to match with self-hosted solutions.
• Flexible Data Residency: For organizations with strict compliance requirements, Atlassian Cloud offers data residency options in multiple regions, directly addressing Atlassian Cloud security compliance concerns for regulated industries.

According to Gartner, by 2025, over 85% of organizations will embrace a cloud-first principle, and 95% of new digital workloads will be deployed on cloud-native platforms – further validating the strategic shift toward cloud solutions like Atlassian’s.

If you’re managing change resistance during your migration, use the proven ADKAR Model for Effective Change Management for communication, leadership engagement, and sustainable adoption across teams.

Pre-Migration Planning & Governance

Building Your Migration Squad

A successful migration requires a dedicated team with clearly defined roles:

• Executive Sponsor: Provides organizational support and resolves cross-department conflicts
• Project Manager: Orchestrates timeline, resources, and communication
• Jira Administrator: Brings technical expertise on configuration and data structures
• Security Lead: Ensures compliance and governance requirements are met
• Quality Assurance: Tests functionality and validates data integrity
• Communications Lead: Manages stakeholder updates and user training

For a best-practice enterprise approach and checklist coverage, see our DevOps Migration Planning Guide, which includes ALM risk assessment, downtime strategies, and post-migration validation.

Data Center Migration Specifics

• Determine if consolidation of multiple nodes or projects is beneficial before exporting to Cloud
• Establish freeze windows for configuration changes during assessment and migration phases
• Create comprehensive snapshot backups before beginning any migration activities
• Validate your load balancer and database configurations to ensure a clean export state

Atlassian Cloud Migration Checklist

Use this comprehensive checklist to guide your preparation:

1. Inventory all Server & Data Center products and their current versions
2. Map user directories and understand existing SSO implementations
3. Audit marketplace apps and verify Cloud availability for each
4. Clean up inactive projects, spaces, and unused custom fields
5. Evaluate custom field complexity and workflow designs for Cloud compatibility
6. Determine data residency and compliance requirements for your organization
7. Calculate storage footprint including attachments, avatars, and historical data
8. Develop comprehensive communication plan for all stakeholders and end-users
9. Schedule pilot testing windows with representative user groups
10. Define clear success criteria and establish a rollback plan if needed
11. Create performance baselines to compare post-migration metrics
12. Arrange support coverage with Atlassian or partners for migration day
13. Document integrations with external systems that may need reconfiguration
14. Review user license counts and Cloud subscription options
15. Establish governance processes for the new Cloud environment

Following this methodical approach will significantly reduce migration risks and ensure you’ve addressed all critical aspects before beginning the actual data transfer.
Cloud migration methods for Jira

Choosing the Right Atlassian Cloud Migration Tools

Official Migration Methods

Atlassian provides several official methods for migrating from Server to Cloud, each with specific strengths and limitations:

1. Jira Cloud Migration Assistant (JCMA)

The Jira Cloud Migration Assistant is the recommended approach for most migrations. This free app installs on your Server instance and provides a guided experience, including migration of project configurations, issues, relationships, and preserving permission structures. It supports incremental migrations and provides pre-migration assessment reports.

JCMA handles the complex mapping between Server and Cloud data models, making it the most reliable method for maintaining data integrity during migration.
Cloud migration methods for Jira

2. CSV Import

CSV Import can serve as a fallback method in specific scenarios but comes with caveats such as loss of workflow history, the need for manual custom field recreation, and limited preservation of issue relationships and links. Use only when JCMA is not viable.

3. Site Import via XML

Rarely used except for large single project moves, requiring XML export/import with limited applicability.

For Confluence, the Confluence Cloud Migration Assistant (CCMA) offers similar functionality.

Third-Party Migration Tools

• Project Configurator for Jira: Useful for complex configuration migrations or site merges
• Botron Configuration Manager: Helps with selective configuration transfers
• Revyz: Advanced data backup and restoration capabilities

When dealing with cross-tool migrations or planning to move between different ALM systems, reference our Cross-Platform DevOps Migration Guide for tool selection and workflow alignment best practices.

Technical Considerations

• Rate Limits: Cloud APIs have throughput limitations
• Network Conditions: Stable, high-bandwidth connections needed
• Timing Estimates: Attachments and history can extend migration windows
• Staging Approach: Strongly consider using a staging Cloud site first

Selecting the appropriate tools based on your specific environment and requirements is critical to migration success.

Step-by-Step Jira Server to Jira Cloud Migration Procedure

1. Preparation & Assessment: Execute all planning steps and ensure completion of the migration checklist.
2. Cloud Site Configuration: Set up destination Cloud environment, configure Atlassian Access, SSO, install required apps. See related Atlassian preparation guide.
   To further optimize your cloud setup, use these Atlassian Cloud Performance Optimization Tips.
3. Assessment with JCMA: Install JCMA on Server, generate assessment reports, remediate blockers.
4. Migration Planning: Select projects, map users/groups, configure permissions and app data migration.
5. Dry-Run Migration: Execute trial migration to sandbox, validate integrity, refine migration plan.
6. Validation Testing: Test workflows, permissions, integrations, dashboards in the sandbox.
7. Migration Preparation: Communicate timeline, schedule downtime, set Server to read-only.
8. Production Migration Execution: Execute, monitor progress, document errors, maintain stakeholder communications.
9. Post-Migration Verification: Re-index Cloud site, finalize app data migration, verify access, test workflows.
   For comprehensive benchmarking, see the Enterprise DevOps Maturity Assessment Guide.
10. Server Decommissioning: Retain Server in read-only, document migration, archive backups, plan license discontinuation.

Common Migration Errors & Solutions

• ERROR VELOCITY-123: Indicates template issues; check custom fields.
• User Mapping Failures: Solve by manual mapping.
• Attachment Migration Issues: Break migrations into batches.
• App Data Migration Failures: Contact app vendors for utilities/support.

Following this structured approach minimizes risk and ensures a controlled transition to your new Cloud environment.

Step-by-Step Confluence Server to Cloud Migration

1. Install CCMA on your Server or Data Center instance.
2. Space Selection and Planning: Prioritize, consider incremental approach, and review permissions.
3. Attachment Transfer Management: Evaluate attachment volume, plan bandwidth, clean up obsolete files.
4. User and Permission Mapping: Ensure account presence, map groups, validate restrictions after migration.
5. Macro Compatibility Assessment:
   

   Macro	Compatibility Issue	Cloud Alternative
   Scroll PDF	Not available in Cloud	Atlassian Document Export
   Refined Toolkit	Different version for Cloud	Refined for Cloud
   Custom HTML/CSS	Restricted in Cloud	Supported HTML subset
   User Macros	Not supported	Forge custom apps
   Advanced Jira Charts	Differences in implementation	Standard Jira charts

6. Space Key Collision Management: Rename duplicates, resolve broken references, check integrations.

Following these guidelines will address the unique challenges of Confluence Server to Cloud migration projects.

Security & Compliance in Atlassian Cloud

Compliance Certifications

• ISO/IEC 27001: Information security management systems
• ISO/IEC 27018: PII protection
• SOC 2 Type II & SOC 3
• GDPR Compliance
• FedRAMP Moderate (U.S. Government)
• PCI DSS for Trello Enterprise

Certifications are regularly audited and updated. Atlassian Trust Center

For embedding security practices throughout your migration & DevOps lifecycle, see our GitHub Advanced Security Implementation Guide.

Encryption & Data Protection

• Data in Transit: TLS 1.2+
• Data at Rest: AES-256
• Key Management: Robust rotation/management

Monitoring & Governance Tools

• Audit Logs: Monitor user/system activity
• Admin Insights
• Atlassian Access: SAML/SCIM identity management

Data Residency Options

• United States
• European Union
• Australia
• Germany
• Roadmap: Canada, UK

Shared Responsibility Model

• Atlassian: Infra/app security, availability, patches
• Customers: User access, app governance, internal compliance

Security Best Practices Checklist

• Enforce multi-factor authentication for all users
• Apply least privilege to group memberships
• Regularly audit API tokens and remove unused integrations
• Implement IP allowlisting
• Enable advanced user provisioning via SCIM
• Configure org-wide security policies
• Schedule access reviews for sensitive projects
• Monitor audit logs for unusual activities

Adhering to these security practices will maintain or exceed enterprise security levels post-migration.

Post-Migration Performance & Optimization

Understanding Cloud Performance Factors

• Geographic network latency
• Browser caching
• Impact of third-party apps
• Instance size (users, projects, storage)

For advanced optimization strategies, visit Mastering Azure DevOps Performance Optimization.

Atlassian Cloud Performance Optimization Tips

• Leverage Atlassian Edge: Regional traffic routing via edge data centers
• Smart CDN: Optimizes static content delivery
• Dashboard Optimization: Limit complex gadgets/JQL filters
• Archive stale data: Use Jira’s Issue Archiving
• App selection: Prefer Forge-based apps for performance
• Monitor: Use Atlassian Analytics & UEM tools

Measuring End-User Experience

1. Open browser developer tools (F12)
2. Check Network tab for “DOMContentLoaded” & “Load” times
3. Report consistently slow performance with captured metrics

Regular audits and user feedback are essential for ongoing optimization.

Comparative Analysis Recap

Decision Matrix: Cloud vs Server

Factor	Atlassian Cloud	Server/Data Center
Cost Structure	Subscription-based (OPEX)	License + infrastructure (CAPEX)
Control	Limited administrative access	Full system control
Compliance	SOC2, ISO, FedRAMP available	Custom compliance implementations
Performance	Managed by Atlassian	Self-optimized
Customization	App-based extensions	Unlimited customization potential
Maintenance	Automatic updates	Manual update planning
Scaling	On-demand	Manual capacity planning
Security	Shared responsibility	Fully self-owned

If your team is conducting an enterprise-wide DevOps assessment post-migration, see our Optimizing Enterprise DevOps Practices with a Comprehensive Maturity Assessment Guide for KPI benchmarking and tool rationalization.

Organization Persona Examples

Regulated Financial Institution: May choose Data Center for custom audit controls, integrations, and regulatory risks.
Fast-Growing Technology Startup: Ideal for Cloud—gain reduced overhead, global access, and scaling.

Total Cost of Ownership Example

Approach	Three Year Total Cost
Data Center	$503,500
Cloud	$397,500

Potential 21% cost reduction (excl. migration).

Case Studies & Success Stories

Global Manufacturing Company: Consolidation Success

• 35% reduction in infrastructure costs
• Elimination of version inconsistencies
• Improved collaboration across 12 countries
• Standardized workflows and reporting

Early app compatibility assessment and sandbox testing were key.

Government Agency: Compliance-Focus Transition

• Improved security audit scores by 28%
• Reduced authorization maintenance workload
• Streamlined contractor onboarding
• Enhanced disaster recovery capabilities

See Atlassian’s official cloud migration case study.
For more on multi-tool migration, refer to our Azure DevOps to GitHub Enterprise Migration Guide.

Conclusion & Next Steps

Execution of a seamless Jira Server to Jira Cloud migration relies on thorough Atlassian Data Center migration planning and strict adherence to your Atlassian Cloud migration checklist. Well-prepared organizations enjoy smoother transitions and fast time-to-value.

For complex requirements, consider engaging Atlassian Solution Partners or Atlassian Migration Support for expert guidance.

If you’re adopting DevOps at scale, see our Enterprise DevOps Adoption Roadmap Guide for best practices in transformation and change management.

The transition to Cloud is an opportunity to reimagine workflows, streamline operations, and unlock continuous innovation from Atlassian’s platform.

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