Zero-Downtime Jira Server to Cloud Migration for a 280-User SaaS Company
The Challenge
A fast-growing SaaS company was running Jira Server 8.x with 47 Marketplace apps, 12,000 issues, and a heavily customised permission scheme. Their IT team had attempted a migration internally and failed twice — each time losing custom field data and breaking automation rules. They needed the migration completed before their Server license expired.
Our Approach
- 1.Audited all 47 apps — 31 had Cloud equivalents, 9 had partial parity, 7 had no Cloud version and needed replacement
- 2.Ran 3 complete dry-run migrations over 3 weeks, fixing data integrity issues at each stage
- 3.Built a custom field mapping document and pre-configured the Cloud instance before cutover
- 4.Replaced 7 unsupported apps with native Jira Automation rules, eliminating licensing costs
- 5.Executed production cutover on a Saturday night — 4.5 hours total with zero issues
Results
"After two failed internal attempts we were nervous. Altosyn ran the whole thing like a machine — the planning phase alone was worth the engagement."
— Head of Engineering, SaaS company (UK)