Purple Teaming in the Real World: When Everything Goes Off the Rails (and That’s Normal)
People love the glossy version of purple teaming:
Everyone aligned, infrastructure ready, dates locked in, testing smooth, reporting clean.
Nice idea. Doesn’t happen.
Here’s how our latest adversarial emulation actually unfolded and why newer folks need to understand that this kind of chaos is completely normal.
We Started Strong
The red team and blue team were perfectly aligned going in. We defined:
The TTPs that mattered
The logging and alerting gaps that the IR team was worried about
What we wanted to trigger
What we expected to at least show up in the logs
A timeline that seemed realistic
A clean RoE
The engagement was mapped out months in advance.
Back at the start of the year, it all felt reasonable and well-planned.
And then reality stepped in.
The Delay Train Arrives
The infrastructure team got hit with a massive company-wide initiative. Completely unplanned when we originally scoped this project. They were already stretched thin, juggling priorities, and then here we come, asking them to build infrastructure in production for us.
They weren’t dragging their feet, they were overwhelmed.
So:
Delay #1: Infrastructure didn’t get built on time.
Delay #2: When it finally went live, we didn’t have permissions to do anything with it.
Delay #3: Every new action revealed a new permission blocker, which meant a new ticket, and more waiting.
And here’s the part that stung a little:
Every time we hit an infrastructure issue, we had to go back to the same infrastructure folks… again!
We knew how slammed they were.
We knew how much was on their plate.
And every “hey, sorry, but we need one more thing” message felt like we were poking someone who was already juggling flaming chainsaws.
But we still had to ask because we still had a job to do.
We couldn’t test without access, and we couldn’t magically create permissions ourselves.
It was uncomfortable, but unavoidable.
The “Test Whatever We Can Today” Phase
The engagement slowly turned into a buffet where we only got to eat whatever dishes happened to be available that day.
Do we have everything required to conduct this test case today? Cool, run it.
Are we missing something that prevents the test case from running? Add it to the ticket pile and pivot to something else.
It was messy.
It was non-linear.
It was the opposite of the beautiful timeline we had anticipated.
We eventually blew past our original deadline by almost two weeks! Not because anyone slacked, but because the environment simply wasn’t ready and everyone was stretched thin.
We Still Got the Work Done
Even with the chaos, things gradually came together.
Permissions started landing.
Infrastructure was stood up.
More pieces unlocked.
We ran every test case, just not in order, and definitely not smoothly.
But we ran them.
We found the visibility gaps.
We gave our incident response team a clear picture of where they were blind.
The engagement delivered real value. We just ended up taking the scenic route.
If You’re New to This Field
Purple teaming rarely goes how you think it will.
Adversarial emulation is rarely clean.
Real orgs operate in real conditions. Shifting priorities, shared responsibilities, overloaded teams, surprise initiatives, and resource crunches.
You will run into:
Permission issues
Missing infrastructure
Delays
Unexpected blockers
Competing priorities
People who want to help but literally don’t have the bandwidth
Test-case issues
It’s not a failure.
It’s not a sign you’re doing something wrong.
It’s simply how these engagements work in the real world sometimes.
Ways to Make Future Engagements Hurt Less
We can’t control everything, but we can learn from it.
Build real buffer time
Not a few days. Actual buffer. Weeks!
Get access validated long before testing begins
If you’re touching the environment for the first time on Day 1, you’re already behind.
Break infra requests into small, digestible chunks
Make it easy for busy teams to help you.
Test in whatever order the environment allows
Forward momentum keeps things alive.
Document blockers as real findings
Permissions, missing agents, missing logs, they’re part of the engagement story.
Acknowledge that some delays are simply uncontrollable
When we planned this early in the year, no one knew a company-wide initiative would land on top of everything. Sometimes timing just works against you.
The Honest Part
This engagement was frustrating.
It was chaotic.
It forced constant adaptation.
And it wasn’t the sleek, well-oiled purple team machine people imagine.
But that’s real-world security.
Attackers don’t wait.
Infrastructure teams don’t magically clear their schedule.
And purple teams don’t get perfect conditions.
The value is in navigating the mess and still producing something meaningful on the other side.
If you’re newer to this work, just know:
It won’t always be smooth.
Sometimes it’s two weeks of “access denied” messages and a constant feeling of “sorry to bug you again…”
But the mission gets done and that’s what truly matters. Make sure to show the folks that are going above and beyond to help you with your engagement some recognition. Let their bosses know how awesome they are!