Before We Migrate: Understanding the Impacts of Jira Cloud Migration Assistant

Most Jira migrations don’t go sideways because the tool fails.

They go sideways because expectations were wrong.

There’s a persistent assumption that the Jira Cloud Migration Assistant simply copies your instance from Data Center into Cloud. Same structure. Same behavior. Different hosting model.

But that’s not what happens.

JCMA translates. And translation always involves interpretation.

Workflows may look similar but behave differently. Permissions may map correctly but feel different to users. Fields may exist but show up in unexpected contexts. None of that means the migration failed — it means the environments aren’t mirrors.

In this week’s article, I break down what the migration assistant actually does, what it absolutely does not do, and why your first migration run should be treated as a diagnostic exercise — not a finish line.

If you’re planning a move to Cloud, understanding this distinction changes everything.

Before You Migrate Anything: Understand What Jira Is Really Being Used For

Most Jira migrations don’t struggle because the data won’t move.
They struggle because nobody stopped to ask what the data actually means first.

Every admin thinks they know their instance. And honestly, they probably know it better than anyone else in the company. But knowing how Jira is configured isn’t the same as knowing how it’s really being used. Old projects stick around. Fields collect dust. Workflows solve problems nobody remembers having. Then the day you move to Cloud, all of that becomes real again — in front of users who now assume you intended it.

Before choosing tools, timelines, or even strategy, there’s a much simpler (and much harder) step: figuring out what matters and what just survived long enough to look important.

This week’s article is about replacing assumptions with evidence — and why that changes the entire migration conversation.

Choosing Your Migration Strategy: Big Bang, Phased, Greenfield, or Hybrid

Once it’s accepted that a Jira Data Center to Cloud move is coming, the next question tends to show up fast: how should it actually happen? That’s usually where things start to speed up a little too much. Dates get floated. “Big bang” gets mentioned. And suddenly a decision that deserves real thought starts feeling like a race.

This post digs into the most common migration strategies — big bang, phased, hybrid, and even the occasional greenfield reset — and, more importantly, when each one actually makes sense. There isn’t a single right answer, because organizations, teams, and Jira instances aren’t interchangeable.

If you’re in the middle of these conversations right now, or know they’re coming soon, this one is about slowing things down just enough to choose intentionally instead of reactively.

Curious which approach feels most realistic where you are right now — or which one stakeholders are pushing for?

The Road Ahead: Why Data Center Migration to Cloud Matters (and What to Expect)

Doing nothing isn’t an option anymore.

Jira Data Center has a real end date, and ignoring it doesn’t make the work go away — it just pushes the pain further down the road.

This article is about what this moment really means for Jira admins, why “lift and shift” thinking falls apart fast, and how to start planning without overreacting.

If you own Jira, this is a conversation worth having now, not in 2028.

So Long, Data Center

Atlassian is ending Data Center, with full shutdown in Mar 2029, and many customers face more than a few hurdles before then. While Cloud offers growth and new features, the transition will be tough for admins and partners, even as migration demand brings fresh opportunities.

This is Why We Can’t Have Nice Screens

Have you ever wondered why the bad custom field advice is terrible?
Like why can’t we have:
– Duplicate field names? Yes, please.
– Required everything? Obviously.
– Free text forever? Why not.
Come for the bad advice, stay for the what will actually happen.

Atlassian Increasing DC prices…again.

Atlassian DC prices are going up. It’s not news at this point. It was even leaked on Reddit late last year (and the post has since been deleted). It seems Atlassian is at least listening, as they are trying to head off some of my old arguments ahead of time in their FAQ. Join us as we discuss what you need to know about this announcement!
What do you guys think? Will these price increases make DC too expensive for even more customers? Please let me know! #AtlassianCreator

A New Era at The Jira Guy

thejiraguy.com has now been around for five years now…and to be honest, we need a change. So, it’s taken a bit, but I’m happy to announce I’m bringing on some new people to help write articles! What do you want to hear about?

Lightweight ways to customize Jira

This week, The Trello Queen herself gets her hands dirty in Jira, showing you some quick and easy ways you can customize Jira to your team’s benefit. What are some ways you’ve customized Jira?

Backing Up Jira Cloud

Have you ever been in a situation where your Jira Cloud data just went poof? If it’s Atlassian’s fault your covered, but what if it’s not? Today we discuss the elements of a healthy backup regime and how you can achieve it with your Jira Cloud Instance.

Paid partnership with Revyz.