The Azure Design Decision That Cost the Most to Undo
A Reflection Written With Equal Parts Humor and Regret
Every Azure architect has one. The decision that looked clean, elegant, and efficient at the time. The one that made sense in the meeting, fit perfectly on the diagram, and shipped right on schedule. The one you now recognize instantly as *the* decision that aged like unrefrigerated milk.
Mine started with confidence. The dangerous kind.
It was early in the journey. The environment was small. The roadmap was optimistic. The phrase “we can always refactor later” was spoken aloud, which should have triggered a fire alarm. We made a foundational Azure design choice based on what was easiest to deploy, not what would be easiest to live with.
At the time, it worked beautifully. Resources deployed quickly. Access was simple. Governance was “lightweight.” The business was happy. The engineers were fast. The architecture diagram looked so clean it could’ve been framed.
Then the organization grew.
And grew.
And acquired another company.
And added compliance requirements.
And introduced more teams.
And suddenly that elegant decision became the single thing everyone worked *around* instead of *with*.
Undoing it turned out to be wildly more expensive than making it.
The real cost wasn’t technical. Azure will happily let you rebuild almost anything if you throw enough time and money at it. The cost was operational. Every system depended on the decision. Every team had built assumptions around it. Every automation pipeline had quietly encoded it as truth.
Changing it meant touching everything.
Identity broke in creative ways. Permissions that had “just worked” stopped working because they were never actually designed. Networking changes rippled through services that didn’t know they were coupled. Governance controls suddenly mattered, and nobody remembered why certain exceptions existed in the first place.
Each attempted fix revealed another hidden dependency. Each dependency revealed another team. Each team revealed another reason why “now isn’t a good time.”
The Azure bill didn’t spike immediately. That would have been obvious. Instead, the cost showed up in meetings. In risk registers. In delays. In security reviews that took weeks instead of hours. In migrations that required three dry runs and a weekend rollback plan.
Engineers burned time compensating for the decision instead of improving the platform. Security added controls that felt hostile because the architecture couldn’t support nuance. Audits became negotiations. Leadership stopped asking when things would be done and started asking why everything felt so fragile.
The most painful part was realizing the decision wasn’t wrong.
It was premature.
It was optimized for speed in a moment when stability, scale, and governance hadn’t yet earned their seat at the table. Azure didn’t fail us. Our assumptions did.
Undoing the decision required more than refactoring. It required re-educating teams, re-aligning ownership, and re-writing unwritten rules. The technical work was measurable. The cultural work was not.
And yes, we eventually fixed it. Slowly. Carefully. With far more planning than the original design ever received. The new architecture was better, more resilient, and far less exciting to look at.
Which is how good architecture usually ends up.
The lesson wasn’t “never move fast.” It was “know which decisions are expensive to reverse.” Subscription models. Identity boundaries. Network topology. Governance hierarchy. These aren’t implementation details. They’re commitments.
Azure makes it easy to start.
It does not make it cheap to change your mind later.
The design decision that cost the most to undo wasn’t a bug or a misconfiguration.
It was assuming future complexity would politely wait its turn.
It never does.
And now, every time I hear “we can always fix it later,” I smile, nod, and quietly ask one question.
“How much later are we willing to pay for?”