Key Challenges & Context: Preparing a Complex Jira Estate for the Cloud
The client had a clear objective: migrate its Jira Software and Jira Service Management Data Center environment to Atlassian Cloud.
The challenge was the scale and complexity of the existing platform. Over a decade, the environment had accumulated extensive configurations, automation, applications, and integrations.
The estate included:
- 932 Jira projects
- 889,552 issues and 2.17 million comments
- 387,118 attachments
- 337,000 Assets CMDB objects
- Around 420 ScriptRunner scripts
- 40 Marketplace applications
- 5,003 user accounts and 3,591 groups
The platform was also connected to systems including Azure DevOps, Jenkins, Power BI, Xray, EasyVista, and Control-M.
This meant the migration could not be approached as a simple move to Cloud. Each application, script, account, workflow, permission, and integration had to be assessed first.
The client also needed to understand which configurations could move directly, which required modernization, and where risks could affect business continuity.
At the same time, user directories contained duplicate accounts and invalid email addresses. Licensing also needed to reflect actual usage before moving to Cloud.
Before committing to migration, the client needed a clear view of its current environment, its Cloud readiness, and the effort required. They also needed a phased roadmap covering security, applications, migration batches, and risk mitigation.
Our Approach: Turning a Complex Jira Estate Into a Clear Cloud Migration Plan
The client needed more than a technical compatibility check. With 932 projects, 40 Marketplace apps, hundreds of ScriptRunner scripts, and years of configuration, they first needed to understand what could move, what had to change, and where the main risks were.
We structured the engagement around Atlassian’s MAGIC 5 framework to assess Cloud readiness across all five dimensions. This gave the client a consistent way to review the environment before defining the migration path.
1. Mapped the existing Jira and JSM environment
We analyzed the client’s Jira Software and Jira Service Management landscape in detail, covering projects, workflows, permissions, automation, and Assets schemas.
The scale made this step essential. The estate included 889,552 issues, 2.17 million comments, 387,118 attachments, and 337,000 CMDB objects. Understanding these dependencies helped create a factual baseline for the migration.
2. Assessed applications, scripts, and integrations
The environment relied on 40 Marketplace apps and extensive customization. We reviewed each application for Cloud compatibility, possible migration paths, and modernization requirements.
This included applications such as ScriptRunner, Xray, BigPicture, EazyBI, Assets, Tempo, and Rich Filters. We also assessed around 420 ScriptRunner scripts and integrations with systems including Azure DevOps, Jenkins, Power BI, EasyVista, and Control-M.
Rather than assuming that existing configurations could simply be recreated in Cloud, we identified where specific constraints needed to be addressed before migration.
3. Reviewed identity, licensing, and data readiness
A Cloud migration also required the client to prepare its user base and subscriptions.
We reviewed 5,003 accounts and 3,591 groups, including user directories, licensing, duplicate accounts, and invalid email addresses. This work identified 134 duplicate accounts and 40 invalid email addresses before they could create problems during migration.
It also gave the client a clearer basis for aligning future Cloud subscriptions with actual usage.
4. Defined the Cloud target and migration roadmap
Once the current environment and its constraints were understood, we translated the findings into a phased migration roadmap.
The roadmap covered migration batches, security, Atlassian Guard, application strategy, required effort, and risk mitigation. It also defined modernization paths for the applications that could not move to Cloud without changes.
This approach gave the client a structured view of what needed to happen before, during, and after migration, while reducing uncertainty around one of the most complex parts of the project.
Benefits: Reducing Migration Risk Before Moving to Cloud
The assessment gave the client a clear view of what needed to be addressed before starting the Cloud migration.
By reviewing the full environment, we identified issues that could have created delays or complications later in the project:
- 134 duplicate user accounts
- 40 invalid email addresses
- 40 Marketplace apps requiring defined migration or modernization paths
- Around 420 ScriptRunner scripts requiring assessment
- 5,003 accounts and 3,591 groups reviewed for Cloud readiness and licensing
This work reduced uncertainty around a migration involving 932 projects, 889,552 issues, 2.17 million comments, 387,118 attachments, and 337,000 CMDB objects.
The client also gained a phased migration roadmap covering migration batches, security, Atlassian Guard, application strategy, effort, and risk mitigation. This provided a structured basis for planning the move to Atlassian Cloud instead of approaching the estate as one large migration.
Reviewing accounts and groups also gave the client the information needed to align future Cloud subscriptions with actual usage. At the application level, the assessment defined modernization paths for tools including ScriptRunner, Xray, BigPicture, EazyBI, Assets, Tempo, and Rich Filters.
The engagement therefore delivered something essential before migration began: a detailed understanding of the current estate, the risks to address, and a practical path toward Cloud.
The source material does not report post-migration performance, cost savings, or operational KPIs, so these outcomes should not be presented as achieved results.
Planning Your Jira Cloud Migration?
If you are preparing a complex Jira Software or Jira Service Management migration to Atlassian Cloud, a clear readiness assessment can help identify risks before they affect the project.
