How to Successfully Upgrade Your Atlassian Products to the Cloud with a Strategic Process
Navigating an upgrade to Atlassian Cloud requires careful planning and expert execution. Whether you're moving from Data Center to Cloud or consolidating multiple instances, a structured approach is essential for minimizing disruption and maximizing value. Isos Technology's proven methodology delivers consistent results by combining technical expertise with strategic planning to ensure your Atlassian upgrade succeeds. This comprehensive guide outlines the step-by-step process for seamlessly migrating data and upgrading your Atlassian products while maintaining data integrity and business continuity.
Key Takeaways
- Strategic Planning is Essential: Successful Atlassian Cloud upgrades require comprehensive assessment and detailed planning that addresses both technical and organizational factors.
- Choose the Right Approach: Upgrade strategies should align with your organization's size, complexity, and business objectives, with different methods appropriate for different scenarios.
- Preparation Drives Success: Thorough environment preparation, including data cleanup and user management, significantly reduces upgrade risks and complications.
- Expert Guidance Matters: Partners like Isos Technology bring specialized expertise and proven methodologies that streamline complex transformations and address challenging scenarios.
- Change Management is Critical: Technical success must be paired with effective user adoption strategies to realize the full benefits of Atlassian Cloud.
Understanding the Atlassian Landscape
The Atlassian ecosystem continues to evolve, with Cloud becoming the strategic platform for organizations seeking enhanced collaboration, reduced maintenance, and improved scalability. An upgrade to Atlassian Cloud represents more than a technical transition—it's a strategic business decision that affects workflows, governance, and organizational efficiency.
Isos Technology approaches Atlassian Cloud upgrades with an outcome-driven methodology that prioritizes business continuity and user experience. As an Atlassian Platinum and Enterprise Solution Partner, Isos brings decades of expertise to help organizations navigate complex transitions while minimizing risk.
Every technology upgrade is unique and requires focused expertise to ensure a seamless cutover. Isos' approach combines technical knowledge with strategic planning to deliver upgrades that align with business objectives while maintaining data integrity.
Step 1: Discovery and Assessment
The foundation of any successful Atlassian Cloud upgrade begins with comprehensive discovery and assessment. This initial phase involves analyzing your current environment, understanding business requirements, and identifying potential challenges.
During discovery, Isos Technology conducts a Cloud Readiness Assessment to evaluate your existing Atlassian implementation. This assessment examines critical factors including:
- Current instance size and complexity
- Custom workflows and configurations
- Installed apps and integrations
- User management systems and authentication methods
- Data governance requirements
- Compliance considerations
The assessment provides clarity on transformation scope, potential challenges, and recommended approaches. For large, complex upgrades, Isos usually performs a Cloud Readiness Assessment to help organizations understand the level of effort and duration of the transition. During this process, we will uncover the legacy artifacts, integrations, and customizations that are essential to understand in order to have a successful upgrade.
This methodical approach ensures all technical and business considerations are addressed before the upgrade begins, establishing a solid foundation for the entire process.
Step 2: Developing a Comprehensive Upgrade Strategy
After thorough assessment, the next step involves creating a detailed upgrade strategy that addresses your organization's specific needs. This strategy defines the approach, timeline, resource requirements, and risk mitigation plans.
There are multiple cloud upgrade methods, including:
- Lift and shift (recommended for organizations with fewer than 10,000 users)
- Phased (for larger, more complex environments)
- Fresh start (for organizations seeking to rebuild their instance)
Isos Technology helps determine the optimal approach based on your organization's size, complexity, and business requirements. Our expertise ensures the strategy aligns with Atlassian best practices while addressing your unique challenges.
The cloud upgrade strategy addresses key considerations including:
- Data migration priorities and methods
- App compatibility and alternatives
- User management and authentication
- Testing protocols
- Training requirements
- Communication plans
- Rollback procedures
Every organization is unique, and there is no one-size-fits-all approach to migrating Jira, Confluence, Jira Service Management, and your other Atlassian tools. Isos' tailored strategies reflect this understanding, providing a clear roadmap for migration success.
Step 3: Preparing Your Environment for an Upgrade
Proper preparation is essential for minimizing upgrade risks and ensuring a smooth transition. This phase focuses on cleaning up your current environment, preparing users, and establishing the target Cloud environment.
Key preparation activities include:
- Cleaning up obsolete data and customizations
- Validating user accounts and ensuring unique email addresses
- Reviewing and rationalizing installed apps
- Setting up your Cloud site and validating administrative access
- Configuring Single Sign-On (SSO) and user management
- Establishing governance frameworks
- Creating test environments
Isos emphasizes the importance of preparing both technical components and people. With all upgrades, we will examine your Single Sign-On solutions and how to apply your solution to Atlassian Cloud. This comprehensive approach addresses both technical requirements and user experience considerations.
The preparation phase also establishes baseline performance metrics and success criteria, providing clear benchmarks for evaluating upgrade success. This methodical approach minimizes surprises during execution and creates a solid foundation for the upgrade process.
Step 4: Executing the Upgrade with Precision
With thorough planning and preparation complete, the execution phase begins. Isos employs a structured approach to cloud upgrade execution, leveraging Atlassian's migration tools while applying proprietary methodologies to address complex scenarios.
The execution process typically includes:
- Install and Configure Tools: Set up the Atlassian Cloud Migration Assistant for Jira and Confluence on your Data Center instance.
- Perform a Test Migration: Select a small subset of data to migrate as a test before full migration.
- Migrate a single project or space that represents your overall data structure
- Validate test migration results for accuracy and completeness
- Gather feedback from test users and refine the migration plan accordingly
- Run the Atlassian Migration Assistant to transfer core data
- Migrate global templates and configurations
- Transfer spaces, projects, and associated data
- Migrate users and groups based on your selected approach
- Migrate Custom Configurations and Workflows
- Transfer custom fields, screens, and workflows
- Validate configuration integrity in the Cloud environment
- Transfer App Data Using Appropriate Methods
- Use vendor-provided migration tools for app data
- Implement alternative solutions for incompatible apps
- Validate Data Integrity Through Comprehensive Testing
- Verify all migrated data for accuracy and completeness
- Ensure workflows function as expected in the Cloud environment
- Address Issues Through Established Resolution Processes
- Identify and resolve upgrade issues promptly
- Document solutions for future reference
- Conduct User Acceptance Testing
- Engage key stakeholders in validation
- Gather feedback on user experience
- Finalize Cutover Planning
- Establish final cutover schedule
- Communicate timeline to all affected users
Isos has extensive experience, as well as proprietary tooling and scripts, that enable us to upgrade your Atlassian tools quickly and efficiently. Our technical expertise ensures data integrity while our project management approach maintains clear communication throughout execution.
For complex scenarios involving instance mergers or consolidations, Isos applies specialized methodologies. Our expertise in handling these complex scenarios ensures successful outcomes even for challenging transitions.
Step 5: Validating and Optimizing Your Cloud Environment
Following the technical upgrade, thorough validation ensures all systems function as expected in the cloud environment. This critical phase verifies data integrity, functionality, and performance before full production deployment.
The validation process includes:
- Comprehensive data verification
- Functionality testing across all workflows
- Performance benchmarking against established metrics
- User acceptance testing with key stakeholders
- Security and compliance validation
- Integration testing with connected systems
Beyond technical validation, this phase also focuses on optimizing the cloud environment to leverage platform capabilities fully. Isos Technology's approach includes identifying opportunities for workflow improvements, governance enhancements, and adoption of Cloud-specific features.
Isos' expertise in data compliance and business best practices means that your organization will be set up for continued success in Cloud. This forward-looking approach ensures organizations not only upgrade successfully, but also position themselves to maximize the benefits of their Cloud investment.
Step 6: Managing Change and Ensuring User Adoption
Technical success represents only part of the upgrade equation. Equally important is ensuring users successfully adapt to the cloud environment through effective change management and training.
Isos Technology's methodology incorporates comprehensive change management throughout the migration process, including:
- Stakeholder engagement from project inception
- Regular communication about upgrade progress and impacts
- User training tailored to different roles and needs
- Documentation of new processes and capabilities
- Post-upgrade support to address user questions
- Feedback mechanisms to identify and resolve issues
With careful planning and the help of an experienced Atlassian partner, the process can be streamlined, the risk can be minimized, and your organization can begin reaping the benefits that come from strong governance of Atlassian tools as well as from Cloud deployment.
This human-centered approach ensures technical success translates into organizational adoption, maximizing the return on your Atlassian Cloud investment.
Step 7: Post-Upgrade Support and Continuous Improvement
The upgrade journey continues after cutover with ongoing support and optimization. Isos Technology provides comprehensive post-upgrade services to ensure long-term success in Atlassian Cloud.
Post-upgrade activities include:
- Monitoring system performance and addressing issues
- Providing user support during the transition period
- Implementing feedback-based improvements
- Optimizing workflows and configurations
- Identifying opportunities for additional automation
- Planning for future enhancements
Once you're up and running in your new Cloud environment, we'll ensure you're getting the most out of your investment. This ongoing partnership approach ensures organizations continue to evolve their Atlassian implementation to meet business needs as they evolve.
The post-upgrade phase also establishes governance frameworks for managing the cloud environment effectively, ensuring sustainable success beyond the initial transition.
Detailed Step-by-Step Cloud Upgrade Instructions
Pre-Upgrade Checklist
Before beginning the upgrade process, complete these essential preparation steps:
- Update Your Data Center Instance
- Ensure your Atlassian Data Center products are on the latest supported versions
- Install the latest version of the Atlassian Cloud Migration Assistant
- Allowlist required IPs and domains for upgrade tools
- Verify User Accounts
- Ensure all users have unique email addresses
- Deactivate or remove inactive user accounts
- Plan user management and authentication approach for Cloud
- Evaluate Apps and Integrations
- Inventory all installed apps and customizations
- Check app compatibility with Atlassian Cloud
- Identify alternatives for incompatible apps
- Contact vendors for upgrade support if needed
- Clean Up Your Environment
- Archive or delete obsolete projects and spaces
- Remove unnecessary custom fields and workflows
- Clean up user groups and permissions
- Establish Upgrade Schedule
- Determine appropriate upgrade timing
- Plan for potential downtime
- Communicate schedule to all stakeholders
Cloud Upgrade Execution Steps
Once preparation is complete, follow these detailed steps to execute your upgrade:
- Set Up Your Cloud Site
- Activate your Atlassian Cloud site if not already established
- Configure basic settings and global permissions
- Set up user management and authentication
- Create a Migration Plan
- Open the Atlassian Cloud Migration Assistant
- Select "Create new migration"
- Connect to your destination Cloud site
- Name your migration and select migration stage (production or testing)
- Configure Migration Components
- Global Templates: Choose to migrate global page templates, custom system templates, all global templates, or none
- Spaces/Projects: Select the spaces or projects to include in your migration
- Users and Groups: Choose between migrating all users and groups or only those related to selected spaces
- Apps: Select to migrate all compatible apps or none
- Run a Test Migration
- Select a small representative sample for initial testing
- Execute the test migration
- Validate results and address any issues
- Gather feedback from test users
- Execute Full Migration
- Perform final backups of all Data Center data
- Start the migration process using the Migration Assistant
- Monitor progress and address any issues
- Validate data as migration completes
- Verify Migration Results
- Conduct a thorough audit of migrated data
- Verify functionality of workflows and customizations
- Test integrations with connected systems
- Validate user access and permissions
- Finalize Cloud Configuration
- Configure Cloud-specific settings
- Set up automation rules
- Optimize workflows for Cloud environment
- Configure app settings and integrations
- Transition Users
- Communicate upgrade completion
- Provide access information to users
- Offer training and support resources
- Gather feedback and address concerns
- Decommission Data Center Environment
- Set Data Center to read-only mode initially
- Maintain for reference during transition period
- Fully decommission after successful adoption
Post-Upgrade Activities
After completing the upgrade, ensure long-term success with these activities:
- Monitor Performance
- Track system performance metrics
- Address any performance issues
- Optimize configurations as needed
- Provide User Support
- Establish support channels for user questions
- Document common issues and solutions
- Offer additional training as needed
- Implement Governance
- Establish Cloud governance frameworks
- Define ongoing management responsibilities
- Document operational procedures
- Gather Feedback
- Collect user feedback on the Cloud experience
- Identify opportunities for improvement
- Implement refinements based on feedback
- Plan Future Enhancements
- Identify opportunities to leverage Cloud-specific features
- Plan for additional automation and integration
- Develop roadmap for continuous improvement
Frequently Asked Questions About Atlassian Cloud Upgrades
What are the key benefits of upgrading to Atlassian Cloud?
Upgrading to Atlassian Cloud delivers numerous benefits including reduced infrastructure maintenance, automatic updates with the latest features, enhanced security, improved scalability, and better integration capabilities. Organizations also benefit from predictable subscription pricing, reduced administrative overhead, and improved accessibility for remote teams. Atlassian Cloud provides built-in compliance with global standards and automatic backups, further reducing operational burdens while improving reliability.
How long does a typical Atlassian upgrade take?
Upgrade timelines vary significantly based on instance size, complexity, and organizational readiness. Simple upgrades with minimal customizations may complete in 4-6 weeks, while complex enterprise transitions to Cloud involving multiple instances and extensive customizations can take 3-6 months or longer. Isos Technology conducts thorough assessments to provide realistic timeline estimates based on your specific environment and requirements, ensuring proper planning and resource allocation.
How should we handle apps and integrations during a Cloud upgrade?
Apps are a critical upgrade consideration. Not all Data Center apps have Cloud equivalents, and some functionalities may differ between versions. Isos Technology recommends conducting a comprehensive app assessment to identify critical functionality, evaluate Cloud alternatives, and develop migration strategies for each app. This may involve migrating app data using vendor-provided tools, implementing alternative solutions, or adjusting workflows to accommodate Cloud capabilities.
What data migration methods are available for Atlassian products?
Atlassian provides several migration methods, with the Cloud Migration Assistant being the recommended approach for most organizations. This tool facilitates "lift and shift" migrations by transferring core data and configurations directly to Cloud. For complex scenarios, Atlassian also supports site import methods and provides APIs for custom migration approaches. Isos Technology leverages these tools while applying proprietary methodologies to address complex migration scenarios not covered by standard tools.
How do we manage user access and authentication during an upgrade?
User management is a critical component of a transition to Cloud. Organizations must ensure all users have unique email addresses and plan for authentication method transitions. Atlassian Access provides enterprise-grade identity management for Cloud implementations, supporting various SSO solutions. Isos Technology helps organizations implement appropriate user management strategies, including SCIM provisioning for automated user synchronization and appropriate permission structures for the Cloud environment.
What testing should we perform before completing the upgrade?
Comprehensive testing is essential for upgrade success. Isos Technology recommends a multi-phase testing approach including functionality testing, performance validation, security verification, and user acceptance testing. Testing should validate all critical workflows, integrations, and customizations using realistic data sets. Establishing a dedicated test environment allows thorough validation without disrupting production operations, while structured test plans ensure all critical components receive appropriate verification.
How can we minimize disruption during cutover?
Minimizing business disruption requires careful cutover planning. Isos Technology recommends scheduling cutovers during low-activity periods and implementing clear communication plans to set user expectations. Establishing instance freezes before migration prevents data loss, while comprehensive rollback plans provide safety nets if issues arise. Phased approaches may be appropriate for large organizations, allowing incremental migration of teams or projects to distribute the impact and allow for adjustments based on early feedback.
What post-upgrade support should we expect?
Effective post-upgrade support ensures long-term success. Isos Technology provides comprehensive support including system monitoring, issue resolution, user assistance, and optimization consulting. Establishing clear support channels helps users navigate the transition, while regular health checks identify opportunities for improvement. Organizations should plan for ongoing governance to maintain the integrity of their Cloud implementation, ensuring continued alignment with business objectives as needs evolve.
How do we measure the success of our Atlassian Cloud upgrade?
Successful Cloud upgrades extend beyond technical completion to include user adoption and business impact. Key metrics include system performance compared to baseline, user adoption rates, support ticket volumes, and workflow efficiency improvements. Gathering user feedback provides qualitative insights to complement technical metrics, while business impact assessments measure improvements in collaboration, time-to-market, and other organizational outcomes. Isos Technology helps establish appropriate success metrics aligned with your upgrade objectives.
What are the most common challenges in Atlassian Cloud upgrades?
Common upgrade challenges include app compatibility issues, data volume complexities, custom workflow transitions, user management hurdles, and change resistance. Isos Technology's experience across numerous Cloud transformations allows them to anticipate and address these challenges proactively. Their methodology incorporates risk identification and mitigation strategies, ensuring potential issues are identified early and addressed before they impact upgrade success.
Sources:
