When Red Tape Meets the Cloud: A Hilariously Anticlimactic Software Cutover
Picture this: You’re part of a lean, four-person dev team, quietly minding your own business in a rogue corner of a Fortune 100 company. Suddenly, the winds of corporate change blow in, and you’re “honored” as the first to move your application to AWS because, well, you’re unimportant. What could possibly go wrong? As it turns out, not the migration itself—but the mountain of red tape towering between you and that sweet, sweet cloud.
It’s a tale of paper-pushing, process inventing, and managers multiplying by the minute. Welcome to the wild world of software cutovers, where a simple deploy gets buried under a bureaucratic avalanche.
Red Tape vs. Reality: A Cloud Migration Comedy
Let’s set the scene. The cloud is all the rage, and your company wants in. ASAP. Your team, a scrappy group used to operating like a startup, gets tapped to blaze the trail. You spin up infrastructure in AWS, keep the old datacenter running just in case, and, shockingly, everything works. You’re ready to cut over.
But then come the managers. And the project managers. And the architects (in title, if not in presence). Suddenly, your streamlined, “just hit deploy” workflow is under a microscope. Corporate wants documentation. Lots of it.
“Document the Deployment Process.”
You stare at the request. The process is: hit “Deploy” on the build server. Done. Apparently, that doesn’t count.
“Document the Rollback Process.”
You’ve never really needed one. If something breaks, you just fix it and deploy again. Sorry, that also doesn’t count.
“Who approves deployments?”
Uh… also you.
“Who’s the architect?”
Do any of you have ‘Architect’ in your job title? No? Well, pick someone anyway.
The PM is not amused. In fact, she’s irate. Every box must be filled, every process must be documented—even if you have to invent it on the spot. So, you and your team play the world’s most awkward game of musical chairs with job titles and responsibilities, just to appease the paperwork gods.
Wrestling the Paperwork Hydra
The real work isn’t the migration—it’s navigating the endless forms. You enlist your manager as the business contact. You pick a coworker to “run the deployment” so you can “approve” it. You dig deep for anyone who could plausibly be labeled an “architect.” You even create a user story in your tracking tool just to have something to point to, knowing full well the PM can’t see it.
Hours go by. The PM, now resigned more than angry, finally gives the green light. The moment of truth arrives.
The Big “Event” (Or, the Lack Thereof)
A huddle of PMs, middle managers, and your weary team assembles on a call, ready for something epic. One by one, the required verbal approvals are given.
Boss: “Yeah, sure.” You: “Yeah, sure.” Coworker: (Deploys.)
Ninety seconds of silence. The deployment works. The migration is done. The call ends.
And that’s it. No fireworks, no disasters, no drama—unless you count the paperwork. You spend more time ticking boxes and inventing processes than actually moving to the cloud.
The Irony of Enterprise IT
What’s the lesson here? Sometimes, the real challenge in tech isn’t the technology—it’s the layers of process and approval that accrue in big organizations. The tools change (hello, AWS), but the bureaucracy remains eternal.
For small, nimble teams, this can feel like being asked to build a rocket ship when all you needed was a bicycle. But in the world of Fortune 100s, every step—no matter how obvious—needs a documented process, a designated approver, and at least one person with “architect” somewhere on their LinkedIn.
Share Your Red Tape Woes!
Have you ever lost hours—or days—to paperwork that seemed to serve no real purpose? Ever had to “approve” your own work, or invent a rollback plan just to fill a form? Drop your stories in the comments! Let’s commiserate about the true trials of tech: not the code, but the process.
And if you’re facing your own cutover, remember: The migration is the easy part. The real hurdle is getting all the signatures.
Original Reddit Post: Red tape: Software cutover edition