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Confluence Server to Cloud: Lessons from an Enterprise Migration

Written by Chris Bland | 19 Jun 2026

When organisations first implement Confluence, it often starts as a simple collaboration platform. Teams create documentation, share knowledge, and collaborate on projects.

Over time, however, Confluence becomes much more than a wiki.

It becomes the organisation's institutional memory.

 

Why a Migration Is About More Than Moving Data

Policies, procedures, project documentation, training materials, knowledge articles, internal communications, and operational processes all accumulate within the platform. Eventually, Confluence becomes so embedded in daily operations that even a few hours of downtime can have significant business consequences.

This was exactly the situation facing the Rainforest Alliance.

Their Confluence Server environment had grown into a business-critical knowledge management platform used daily by more than 1,000 employees and containing hundreds of gigabytes of information. With Atlassian Server reaching end of support, the organisation needed a clear path to Atlassian Cloud while maintaining business continuity.

The challenge wasn't simply moving content.

The challenge was ensuring that users could continue working effectively throughout the migration process.

 

 

The Common Challenges Organisations Face During Confluence Migration

Many organisations underestimate the complexity of migrating Confluence Server to Cloud.

At first glance, it appears to be a straightforward technical exercise. Export data, import data, test, and go live.

In reality, enterprise Confluence migrations often involve:

  • Thousands of pages and attachments
  • Complex permission structures
  • Legacy content that requires archiving
  • Marketplace app dependencies
  • Customisations and integrations
  • Multiple business stakeholders
  • User adoption concerns
  • Governance and compliance requirements

Migration tools can move data, but they cannot decide:

  • Which spaces should be retired
  • How permissions should be modernised
  • Whether apps should be replaced
  • How users should work in Cloud
  • What governance improvements should be introduced

These decisions require business engagement, planning, and experience.

 

Why Communication Is Just as Important as Technology

One of the most overlooked aspects of a Confluence Cloud migration is communication.

Large migrations involve multiple audiences:

  • IT teams
  • Knowledge managers
  • Business users
  • Department leaders
  • Executive sponsors

Each group has different concerns:

 

This was one of the reasons Rainforest Alliance selected BDQ.

As Senior Knowledge Management & Standardisation Officer Cintia Rivera explained, many of the alternative providers they evaluated were highly technical but struggled to communicate with non-technical stakeholders.

Successful migrations require the ability to translate technical complexity into business language.

This is particularly important when gaining executive approval, securing budgets, and driving user adoption.

โ€œWould I recommend BDQ? For sure! For me, an indicator was that when I was busy with other projects that needed more of my attention, I was confident that I could step back and prioritise those other projects because I was reassured that the project with BDQ was going well.โ€

Cintia Rivera | Senior Knowledge Management & Standardisation Officer, Rainforest Alliance

โ†’  Read the full Case Study

 

 

How Trial Migrations Reduced Risk

One of the most effective ways to reduce migration risk is to avoid treating production migration as the first migration.

Instead, organisations should perform multiple migration rehearsals before go-live.

For Rainforest Alliance, BDQ implemented a cloned migration approach that allowed repeated test migrations to be performed without impacting the live production environment.

This delivered several important benefits:

  • Users could validate content before go-live
  • Migration timings could be refined
  • Marketplace app behaviour could be tested
  • Risks could be identified early
  • Downtime could be minimised

The cloned environments could be refreshed throughout the project, ensuring that testing remained representative of the production system.

Rather than hoping everything would work on migration weekend, the organisation already knew what the outcome would be because they had effectively rehearsed it multiple times.

For large Confluence Cloud migrations, this approach significantly reduces uncertainty.

 

User Acceptance Testing:
The Difference Between Success and Frustration

Many migration projects focus heavily on technical testing.

However, technical success does not automatically create user confidence.

A migration may appear perfect from an IT perspective while still creating frustration for business users.

This is why User Acceptance Testing (UAT) is so important.

The challenge is that many users have never participated in structured UAT before.

Questions often include:

  • What should I test?
  • How do I report issues?
  • How do I know if something is wrong?
  • What happens if I find a problem?

Rainforest Alliance recognised this challenge early.

To support adoption, BDQ provided:

  • UAT training sessions
  • Testing guidance
  • Structured feedback processes
  • Issue tracking workflows
  • Review sessions

This enabled users to participate confidently and helped identify issues long before production cutover.

 

Marketplace Apps:
The Biggest Migration Wildcard

Marketplace apps are frequently one of the most complex aspects of a Confluence migration.

Many organisations have spent years enhancing Confluence with apps that support:

  • Reporting
  • Forms
  • Document control
  • Metadata management
  • Workflow automation
  • Diagramming
  • Knowledge management

The problem is that Cloud and Server apps are not always identical.

Some apps:

  • Have different functionality
  • Require alternative configurations
  • Need data migration approaches
  • May not exist in Cloud at all

This is why Marketplace app assessments should be conducted early in any migration project.

According to Atlassian Marketplace data, thousands of apps are available across the Atlassian ecosystem, demonstrating how important extensions have become within enterprise environments.

The larger the Confluence environment, the more important app planning becomes.

 

 

Migration isn't always about cloud

Many organisations assume migration projects only occur when moving from Server or Data Center to Cloud.

Organisations migrate for various reasons:

  • Consolidating multiple Confluence instances after mergers or acquisitions to create a unified and streamlined knowledge base that enhances collaboration and reduces redundancy across the newly combined organisation.
  • Migrating from one work management platform to another to leverage improved features, increase efficiency, and better align with the evolving needs of the business and its teams.
  • Replacing legacy knowledge management systems with modern, more capable solutions that support enhanced search, collaboration, and content management functionalities to better serve users.
  • Standardising on Atlassian products across the business to ensure consistency, improve integration between tools, and simplify training and support for employees.
  • Rationalising tools to improve reporting and governance by reducing the number of disparate systems, thereby enhancing data accuracy and streamlining compliance processes

For example, we've helped organisations migrate work management solutions such as Monday.com into Jira, enabling teams to consolidate reporting, reduce tool sprawl, and create a single source of truth for project delivery.

โ†’ Case Study | BDQ Monday to Jira migration for PartnerHero

 

Although every migration differs, the same principles apply:

  • Understand the business objectives
  • Analyse the source data
  • Design the target environment correctly
  • Test thoroughly
  • Train users
  • Manage adoption

Whether the destination is Atlassian Cloud or another platform, migration success depends on balancing technical execution with business change.

 

Best Practices for Confluence Cloud Migration

Every migration is different, but several best practices consistently improve outcomes.

๐Ÿšฉ Start with Discovery

Before planning the migration, understand:

  • What content exists
  • Who owns it
  • What can be archived
  • Which apps are business-critical
  • How users currently work
๐Ÿงช Test Early and Often

Migration rehearsals reduce uncertainty and identify issues before they become business problems.

๐ŸŽฏ Focus on User Adoption

Training, communication, and support often have more impact than technical migration activities.

๐Ÿ” Review Governance

Migration projects create an ideal opportunity to improve:

  • Space ownership
  • Permissions
  • Content lifecycle management
  • Knowledge management standards
โœˆ๏ธ Treat Migration as Transformation

The goal should not simply be to recreate the old environment in Cloud.

The goal should be to improve collaboration, governance, usability, and knowledge sharing.

 

 

FAQ: Confluence Cloud Migration

Q. How long does a Confluence Cloud migration take?

A. It depends on the size of the environment, the number of Marketplace apps, governance requirements, and testing activities. Large enterprise migrations often involve several rounds of testing before production migration.

Q. Can all Confluence Server apps be migrated to Cloud?

A. Not always. Some apps have direct Cloud equivalents, while others require alternative solutions or redesigned processes.

Q. How much downtime should we expect?

A. With proper planning and migration rehearsals, downtime can often be significantly reduced compared to traditional migration approaches.

Q. Should we clean up Confluence before migrating?

A. Yes. Migration projects are an excellent opportunity to archive outdated content, improve permissions, and simplify information architecture.

Q. Is Confluence Cloud suitable for large organisations?

A. Yes. Atlassian has continued to invest heavily in Cloud scalability and enterprise capabilities, making Cloud suitable for very large environments.

 

 

Final Thoughts

The Rainforest Alliance migration demonstrates that successful Confluence Cloud migrations depend on much more than technology.

Planning, communication, user adoption, governance, testing, and transparency all play critical roles in reducing risk and achieving successful outcomes.

For organisations with large Confluence Server or Data Center environments, migration is an opportunity not only to modernise infrastructure but also to improve the way knowledge is managed and shared across the business.

If you're considering a Confluence Cloud migration and want to understand the risks, app compatibility considerations, governance opportunities, or migration approach that best fits your organisation, we'd be happy to help.

Book a Confluence Cloud Migration Assessment and start building a roadmap for a successful migration.