Jira Cloud migration survey to make a comprehensive plan

Last 3 years (till Feb, 2024), I used a number of questions to migrate from Jira Server to Jira cloud to make migration go smoothly. 

And Of course I used that resources like Migration plan (Complex Cloud migrations))

And Cloud migration guide, and that information with my checklist many migrations passed, of course the first migrations were complicated, today I would say migration to cloud is smooth and easily :) So please read and use my checklist for your migration if you don’t migrate yet.

Migrating from a Jira Server instance to Jira Cloud Enterprise is a significant project that requires careful planning and consideration. Below is a list of categories with corresponding questions that you should address in your migration plan to ensure a smooth transition:

1. Pre-Migration Planning

• What specific outcomes are we hoping to achieve by transitioning to Jira Cloud Enterprise?

• Can we outline a detailed migration roadmap with milestones, deadlines, and a timeline for the entire process?

• Who are the designated members of the migration project team, and can we define each member’s roles and tasks?

• What methods and channels will we use to keep stakeholders and users updated throughout the migration process?

2. Technical Assessment

• What is the current Jira Server version in use, and are there any dependencies tied to this version?

• Could you provide a list of essential apps or plugins used in your server environment, and indicate whether you’ve checked their availability and compatibility with Jira Cloud? (header of file: Name of app, app key, SEN, Expiration date, Installed version)

• Could you provide a list of SEN- numbers of your apps? And expiration date as well. 

• Are there custom integrations or scripts that are integral to your operations, and if so, can you categorize them (e.g., bi-directional, uni-directional)?

• Could you supply configuration details, custom scripts, and screenshots for apps like Scriptrunner, MyGroovy, Jira Misc Custom Fields, JMWE, myGroovy or any other scripting and automation tools in use?

• For apps like Automation for Jira, please provide an inventory of rules and configurations

• What authentication systems are currently in place (e.g., LDAP/AD, SSO/SAML), and do we have details on the integration points?

3. Data and Content Analysis

• Is there an internal documentation repository describing current processes, workflows, customizations, and configurations that we can review?

• Can we acquire statistics on the following:

• Project count

• Issue count

• Workflow count including conditions, validators, post-functions

• Custom field count and usage details, especially for non-standard fields

• Attachment count and total data size

• Count of active users and user groups

• Plugins and js scripts in use

• Any information in announcement banner

• Are there any specific datasets or historical records that can be archived instead of migrated?

• Could you provide a support.zip file for analysis?

• What throughput Internet channel do you have that Jira server to Atlassian cloud? 

• What strategy will be in place to ensure data security and privacy is maintained throughout the migration process?

4. Testing and Validation

• What will our end-to-bind testing look like, and can we simulate the migration in a test environment?

• How will we verify the integrity and completeness of the migrated data, and do we have acceptance criteria defined by stakeholders?

• Can we create and share a migration success checklist from our perspective, complementing the criteria provided by stakeholders?

• How will we track, manage, and resolve any issues that arise during the testing phase?

5. User Management and Training

• What is the procedure for transferring user accounts and permissions to the new Jira Cloud environment?

• What training materials and assistance will be provided to users to facilitate their transition to Jira Cloud?

• How will user access be controlled and managed during the cutover?

• Are there anticipated changes to authentication methods during the upgrade to Cloud that we should prepare for?

6. Migration Execution

• Can we outline a comprehensive, step-by-step action plan for the migration, including key tasks and responsibilities?

• What is our contingency or rollback strategy should we encounter critical issues during migration?

• How much system downtime is anticipated, and how will this be communicated to users and stakeholders?

• Have we established lines of communication with Atlassian Support specifically for the migration? Can we reference any relevant tickets or support IDs?

7. Post-Migration Review

• What mechanisms will we put in place to confirm the migration’s success?

• What predefined criteria must be met before we consider the migration project closed?

• How will we collect and process user feedback post-migration to assess their experience and any issues they encounter?

• Can we document and share lessons learned and best practices for future migrations?

8. Cost Analysis and Budgeting

• How does the Jira Cloud pricing model compare to our current Server costs, and what implications does this have for our budget?

• Have we allocated funds for potential cost increases associated with subscriptions or new Cloud services?

• Are we aware of any additional costs connected to third-party apps or services required within the Cloud setting?

• Do we have an ROI analysis to justify the move to Jira Cloud against our current and projected Server costs? Or better migrate to Data Center 

9. Ongoing Support and Maintenance

• What modifications are needed for our support and maintenance workflows post-migration?

• How will we handle routine Cloud updates and maintenance tasks?

• What kind of monitoring and alert systems do we need to put in place for the Cloud environment?

• How does the Cloud migration affect our existing backup and disaster recovery plans?

10. Legal and Compliance Considerations

• Are we aware of the compliance standards (e.g., GDPR, HIPAA) pertinent to our industry, and how does Jira Cloud align with these regulations?

• What legal concerns, such as data residency or sovereignty, might impact our migration to Cloud, and how will we address them?

• How will we ensure continuous adherence to both internal policies and external regulatory requirements within the Cloud environment?

• Have we reviewed and updated our agreements with Atlassian to reflect our compliance and data protection needs?

To ensure the success of the migration and meet both technical and organizational requirements, it’s essential to engage with stakeholders early, communicate plans and progress effectively, and adapt our approach based on the size and complexity of your Jira Server instance. Please provide any additional information or requirements to customize and finalize the preparation for the migration.

Enjoy, Gonchik!