What are the biggest challenges you've faced while migrating from Jira Data Center to Jira Cloud?

Hi, @jameers 👋 Great question.

From my experience, the biggest DC → Cloud migration challenges are usually:

• Apps and Marketplace plugins as not every DC app has a Cloud equivalent, and even when it does, the features sometimes may differ. App assessment should start as early as possible.

• Legacy configuration cleanup - old workflows, custom fields, schemes, inactive projects, old users and groups… 🦖 Migrating everything as-is usually makes Cloud harder to adopt.

• User and group mapping - especially with multiple directories, inactive users, duplicate accounts, or unclear group naming.

• Integrations - SSO, email handlers, REST/API integrations, development tools, BI tools, etc. These often need redesign, not just migration.

• Automation and permissions - most configurations migrate quite well with the migration assistant, but I would still validate workflows, permissions, notifications, boards, filters, dashboards, and automation rules carefully after each migration.

• Change management - Cloud has different admin, UI, security, and app behaviour. Training and communication matter a lot 💙

What I’d recommend:

• run at least one test migration

• clean up as much as possible before migrating

• assess apps early

• freeze major configuration changes before the final migration

• prepare a clear user communication plan

• validate with real project owners, not only admins

A couple of Community articles/discussions that may also be useful reads:

• Top Jira Cloud Migration Challenges and How to Address Them - good overview of practical migration pain points, not just the technical part.

• The Jira Data Center Migration Blueprint: 10 Best Practices for Moving to Jira Cloud - useful checklist-style article for planning, cleanup, stakeholder alignment, and testing.

• How to Build a Cloud Migration Playbook for Jira and Confluence - nice read if you want a more structured migration plan with responsibilities, timelines, and lessons learned.

• Jira Instance Cleanup Guide - not migration-specific only, but very relevant. Cleanup before migration can save a lot of pain later.

Hope these help 💙 Cloud migration is usually 30% tooling and 70% cleanup, preparation, decisions, and communication 😊

Agree with everything stated above.

Definitely work with a Partner if you can. Coming from an Atlassian Platinum Parter in a previous life, they've seen almost everything under the sun when it comes to Cloud migrations. Plus, Partners have good relationships with many of the major third-party app vendors; Marketplace apps are often the more difficult piece of migrations, so direct access to support can be a life saver.

Second thing I'd say/echo is the best way to think about migrations is that they're more of a transformation. Regardless of your approach (lift and shift all data and apps, or cleanup on prem then migrate), Cloud is a very different platform with many new/different features. UI/UX differences, third-party app differences, etc.

Don't expect everything to work the same way; users will undoubtedly have questions as they get used to the platform. Echoing @Brita Moorus , good training and communication are key.

Last thing, the team working on the migration deserves some grace. Migrations are hard journeys where you often need to pivot plans as you go through discovery, implementation, and even once you're in Cloud. Be kind to yourself (from someone who tends to be my own worst critic).

We did ours with a vendor, and the vendor had done it before so that certainly helped us out a lot.

We did do a lot of clean up beforehand though for all the fields, workflows etc, we took it as a good chance to clean up our system too. We also chose a few key people who were go to amongst teams who were more Atlassian experienced to do testing ahead of time and help other users and do the change management, this helped myself from the Systems team from getting swamped.

A dedicated page (Sharepoint/Confluence) also helped that included basic stuff about the change, cloud UI, youtube videos, who to contact etc. It was sort of lucky the navigation changes came in just before it so Atlassian had a bunch of updated videos due to it that we used as "get started guides" for users.

Security wasn't too bad, but there was the typical assessments, security was harder for marketplace apps though. Particularly ones you can't pin the location of data were big blockers for us. Also we found scriptrunner to not run the same way in data centre. 

Regarding issues we had:

• Single sign on / access - this was a headache for us being in an organisation level. As I can no longer manage users the same way and getting SSO set up and users was and still is a massive headache. Particularly as we have users in other areas Jiras doing stuff to users that affect our areas jiras users (eg. they disable an Atlassian account as the user doesn't work in their department, but it disables in ours too).
• We also had to redo permissions, mapping etc
• A weird one, in data centre we would add say 2 projects into a sprint board/filter and it would appear in both projects. In Cloud you have to choose a single location, this stuffed around a few teams that work on single sprint boards across multiple different spaces.
• A lot of stuff is moved to an organisation admin. This has been a bit grindy for us as I have to wait for their capacity to make changes, and they don't know if the change is okay to make because only I know why we need the change. Even basic things like seeing upcoming bundled changes and I think even full logs were missing?
• Oh and a weird one Confluence had issues, some macros didn't work properly, some images didn't come through. And some weird permissions. I had to manually update some spaces, so keeping the original data centre for a month at least was super helpful. It was also useful because we had users say "this was in data centre I swear" and I could look and see that it wasn't.

I will say though, there wasn't any major issues just things you need to work through.

Oh yeah and two things

1. No matter how many emails, banners, messages and team meetings telling people we are moving to cloud and here is the new URL someone will still come and ask "What happened to our jira?!?! Where did it go?!?!"
2. I recommend making your data center read only after the migration. Because guaranteed someone will continue working in there if you don't.