Once the reality of a Jira Data Center to Cloud migration sinks in, the next question usually follows almost immediately:
“Okay… so how do we actually do this?”
This is often where conversations start to drift from thoughtful planning into reactive decision-making. Someone proposes a date. Someone else suggests a long weekend. Before long, the phrase “big bang migration” gets tossed around like it’s a test of bravery.
Let’s slow that down. Take a deep breath. Breathe out slowly. We have a deadline, but we are not in rush mode…
Your migration strategy is the single biggest factor in whether this transition feels controlled and deliberate — or chaotic and credibility-damaging. Tools matter. Preparation matters. But strategy is what determines how much disruption teams feel and how much trust admins retain when (not if, when) something inevitably doesn’t go exactly as planned.
There is no universally “correct” migration strategy. Instead, what we find is that some strategies fit organizations better than others, and when a strategy fails, it’s often because it was the wrong approach for that organization.
This article looks at the three most common approaches — Big Bang, Phased, and Hybrid — and how to think about choosing the right one for your Jira instance and your teams. We’ll also take a look at the Greenfield approach, which is best characterized as the “Not a Migration” migration strategy. I have a feeling anyone who has ever wanted to just burn down their Jira and start anew will love that approach.
The Big Bang Migration: Fast, Decisive, and Unforgiving
A Big Bang migration is defined as the “move everything all at once” approach. All projects, all users, all configurations are migrated in a single coordinated cutover. Data Center is shut down and Cloud becomes The Jira instance in one decisive moment. I’ve been a part of cutovers in other contexts, and when you are done and things are online, there is a satisfying finality that I’m not going to lie, it is tempting.
Why Organizations Choose Big Bang
Big bang migrations are appealing because they promise closure.
There’s one timeline, one communication plan, and one moment where everyone is told, “This is Jira now.” Leadership often prefers this approach because it feels clean and finite. There’s no prolonged period of running two systems and no ambiguity about where work lives.
From an admin perspective, it can also feel simpler. One migration run. One validation window. One go-live.
And to be fair, big bang migrations can work — particularly when the Jira instance is relatively small, lightly customized, and supported by teams that are already comfortable with change. But funnily enough, the instances that are exactly opposite to this are those most tempted by the allure of a Big Band transition.
Where Big Bang Migrations Break Down
The trade-off is that big bang migrations allow almost no room for error.
If something goes wrong, it goes wrong for everyone at the same time. Support queues spike immediately. Users lose confidence quickly. Rollbacks are complicated. And you did leave yourself a rollback path, right? RIGHT!?
Big bang also eliminates learning loops. Every assumption made during planning is tested in production, in front of the entire organization. You find out the things you didn’t know that you didn’t know live, and you have to come up with solutions on the fly – whether they are optimal or not.
Instances with heavy automation, deep app dependencies, or years of accumulated configuration debt are especially vulnerable here. In those cases, big bang stops being a strategy and starts being a gamble. And it’s important to remember when you gamble, the odds rarely favor you.
If you haven’t picked up on it yet, this is not my ideal approach. It leaves to many open questions that you find out are being asked much too late. Can it work? Yes, in very specific situations. But if you’ve been using Jira for any length of time, while not impossible, it’s an extremely difficult road to travel.
Phased Migration: Slower, Safer, and More Forgiving
A Phased Migration is very much the opposite of a Big Bang Migration. If a Big Bang is the “move everything all at once” approach, a Phased Migration is the “Take everything over a bit at a time.”
A phased migration breaks the transition into smaller, more manageable pieces — typically by project, department, or business unit, or business function. Instead of moving everything at once, a subset of teams migrates first. Their experience informs the next wave, and the approach evolves as lessons are learned. By the time the last teams move and you are ready to retire the Data Center instance, everything should run smoothly and easily.
This is where the Jira Cloud Migration Assistant becomes particularly valuable, since it supports incremental migrations without overwriting existing Cloud data.
Why Phased Migrations Work in Practice
In my opinion, Phased Migrations work for two reasons.
First, remember to back when you were at University. What classes were better to learn in? The giant class with stadium seating where you were one of 60-120 students, where you were just one face among many, or the small class of about 20 students where you knew beyond a doubt that the professor knew you by name?
I find this very analogous. You can take the time to focus on each team or subset. What are their needs? What isn’t working for them in their current configuration? Are they better served being on a large central site, or just one of many smaller sites on your org? What are their “nice to haves,” and how does that inform your site strategy? All these are much easier to answer when you are dealing with a smaller group – instead of trying to deal with them among everyone else in a big bang move.
Second, a Phased migrations create feedback loops. Each wave answers questions that planning alone can’t:
- How do users respond to Cloud differences?
- Which workflows behave differently than expected?
- Where does automation need adjustment?
- What support issues come up most often?
Those insights can be applied to subsequent teams to make make each iteration that much smoother and less risky.
Phased migrations also help build internal advocates. Early adopter teams often become informal champions who can speak credibly to peers about what changed, what didn’t, and what actually mattered. People aren’t hearing it from you – who no matter what you say, they will see as a biased source. Instead they are hearing it from one of their own. That social proof reduces resistance far more effectively than documentation alone.
The Trade-Offs of Going Phased
Phased migrations take longer. Depending on the scale of your instance, it could be MUCH longer. Depending on your team size, you may need to consider running multiple groups in parallel to spead things up. They require clearer governance during the transition and a willingness to run Data Center and Cloud in parallel for a period of time.
There may be confusion about where work lives, pressure to accelerate timelines, or added complexity around integrations.
But the payoff is a much smaller blast radius when issues arise — and more opportunities to correct course before those issues affect everyone.
A Word on Greenfield Migrations
So, have you ever been diagnosing a workflow issue, except you are on your sixth transition between two statuses trying to find the exact one that has a post function that edits the exact variation of some custom field that isn’t working, except there are three different fields with similar names, and because some previous admin wasn’t careful and judicious, of course all three appear in different parts of this workflow, but you have a bandaid automation that keeps all three versions of the field in sync, so it mostly works, except in this one odd edge case…and really you just want to start over with a fresh instance without all this baggage and how people what Jira could really be?
If so, I have a deal for you…
For particularly “messy” instances of Jira, an option you may want to pitch is what is called a Greenfield Migration. If the Big Band migration is the “move everything all at once” approach, and the Phased migration is the “take everything over a bit at a time” approach, A Greenfield migration is the “Do we actually have to migrate anything?” approach.
Greenfield works best in two scenarios.
- First, when history is rarely referenced, existing workflows are clearly broken, or teams want a clean reset.
- Second, when the team in question is not currently using Jira, is ready to start, and you are mid-migration.
This approach reduces complexity, encourages Cloud-native thinking, and avoids recreating past mistakes. It isn’t always possible, but when it is, it can be transformative. There is a certain catharsis in being able to show a team that constantly complains about Jira what you’ve always known: that “No, really, it was the configuration all along, not Jira itself”
Hybrid Strategies: When Reality Gets a Vote
One of my favorite quotes is “Life is what happens when we are busy making other plans.” The reality is that many real-world migrations don’t fit neatly into either category. The fact is that even if you choose one or the other strategy, you are trying to hit a moving target, and that may necessitate you make changes to your planned strategy.
You may consider Hybrid strategies emerge because some teams are ready to move right now, and others are just not there yet because of compliance requirements, business-critical dependencies, or app limitations.
In a hybrid approach, most teams may move to Cloud while a subset of projects remains on Data Center temporarily, with integrations bridging the gap.
You Only Fail When You Give Up
Lets say you started intending a Big Bang Migration, but you find a Business Unit that simply cannot migrate to Cloud because they depend on an app for complience, and there isn’t anything workable for that solution in Cloud yet. Have you failed? Only if you decide “Because I can’t migrate everyone, I can’t migrate anyone.” Adopting a hybrid strategy often isn’t about failing, it’s about course correction. Just because that business unit can’t move, doesn’t mean it has to hold everyone back. It’s not indecision, it’s being responsive to real-world discoveries.
In practice, hybrid strategies often reflect maturity, not hesitation.
The key is intentionality. Hybrid should be time-bound, clearly communicated, and part of a defined plan — not an accidental limbo state that persists indefinitely. You need to make it clear to the teams you are choosing not to migrate that this isn’t a “they get to stay forever,” it’s a “We are going to take a closer look at your use case and find a solution that works for you. It’s just going to take a bit more time.” As we discussed last week, doing nothing is no longer an option, after all.
Choosing the Right Strategy: Questions That Actually Matter
So, how do we decide which approach is right for our organization? Rather than asking which approach sounds best, it’s more useful to ask questions that expose risk.
- How complex is the Jira instance really? Not just in project count, but in workflow variation, automation density, custom fields, app logic, and integrations.
- How tolerant is the organization to disruption? Downtime tolerance, error tolerance, and appetite for change matter more than technical elegance.
- Are there trusted early adopters? Teams that are open to change and willing to provide feedback make phased migrations dramatically more effective.
- How interconnected are teams really? Are the constantly trading work items among projects, or are they fairly siloed?
While these don’t answer the question directly, when taken in conjuction, they can expose what could happen if one Migration Strategy or another fails, and how acceptable is that scenario. And that can often tell you more about which approach to take than any direct question could.
Wrapping It All Up: Strategy First, Always
At this point in the series, two things should be clear.
First, the Jira Data Center end-of-life date isn’t an abstract future problem anymore. It’s a fixed point on the calendar that forces every organization running Jira today to make decisions — whether those decisions happen deliberately or under pressure later on.
Second, how you choose to migrate matters just as much as when you choose to migrate. Big Bang, Phased, Greenfield, and Hybrid approaches all have their place. None of them are inherently “right” or “wrong.” What gets teams into trouble isn’t picking the wrong strategy — it’s picking a strategy without understanding the risks it introduces, the assumptions it makes, and the kinds of failures it’s least tolerant of.
This article is about slowing the process down just enough to make that choice intentionally. Not because there’s infinite time, but because reacting too quickly often creates more work, more disruption, and more frustration than it prevents.
So far in this series, we’ve talked about why doing nothing is no longer an option, and now how to think about choosing a migration path that fits your organization instead of forcing your organization to fit the migration. The next logical step is to get even more grounded.
Next week, we’ll shift from strategy to preparation. Specifically, we’ll look at how to assess the current state of a Jira instance before migration — what’s actually being used, what’s just taking up space, and how tools like Portfolio Insights can replace gut feelings with real data. Because before deciding what to move and how to move it, it’s worth being very clear about what’s still earning its keep.
Until then, this is Rodney, asking, “Have you updated your Jira Issues today?”
The Jira Guy 