What I Learned from That Client Who Waited Too Long

Back in 2014, CTTS was called in to a large professional services firm in downtown Austin. Longstanding organization. Great people. Terrible technology.

Their IT environment was being run on Novell NetWare and GroupWise, which, even back then, was like using a rotary phone in a smartphone world. We saw immediate risks and put together a full modernization proposal. But the decision was sent to the Board of Directors… and that’s where things stalled.

They said they’d “circle back next quarter.”

What I Learned from That Client Who Waited Too Long

While the board debated, the inevitable happened. An intern opened an innocent-looking email that contained a ransomware payload. Within minutes, the intern’s machine was encrypted. Then the file server running on ancient NetWare went down, too, and they had zero backups. Years of client data, legal records, and financials—gone!

We were in full damage-control mode. And because it was 2014, there wasn’t exactly a Bitcoin ATM around the corner. I had to drive to Walmart, wire money to a sketchy exchange, and wait while we jumped through hoops to secure just $500 worth of bitcoin. That’s how we paid the ransom.

CTTS was eventually able to unencrypt the files and build version 1.0 of their new file system and email server—the same one they still use today. But it cost them.

  • The delay cost them over $100,000 in legal cleanup.

  • They lost access to critical documents for two weeks.

  • Client trust took a hit.

  • And every new upgrade after that had to be rushed and reactive.

I’ll never forget what the Chairman of the Board told me a few months later:

“We thought waiting would give us clarity, but it just brought us disaster.”

That stuck with me. And I see versions of this same story play out even today. Businesses wait to modernize their cloud setup. They wait to add proper backups. They wait to enforce MFA. Until something breaks—and suddenly, the budget appears.

Look, I understand boards, budgets, and bottlenecks. But in 2025, waiting too long isn’t strategic—it’s risky.

If it’s been a while since you’ve reviewed your cloud security or backup strategy, don’t wait until something breaks. Let’s talk through your current setup and make sure it’s keeping up with your business.

Call me today at (512) 388-5559 to schedule your next Quarterly Business Review.

We’ll keep you ahead of the game—and out of Walmart’s wire transfer line.

Frequently Asked Questions about Cloud Security

Q. What were the consequences of delaying IT upgrades for the professional services firm in Austin?
A. Delaying IT upgrades cost the firm over $100,000 in legal cleanup after a ransomware attack encrypted their systems. They also lost access to critical client, legal, and financial documents for two weeks, suffered reputational damage, and were forced into a pattern of rushed, reactive technology decisions moving forward.

Q. How did CTTS respond to the ransomware attack, and what steps were taken to recover the data?
A. CTTS acted quickly to manage the crisis. With no modern backup systems in place, the team located and used an unconventional method to acquire $500 worth of bitcoin to pay the ransom. After payment, CTTS successfully unencrypted the firm’s files and built a new file system and email server to modernize their IT infrastructure—an environment the firm continues to use today.

Q. What risks do businesses face today if they delay reviewing their cloud security and backup strategy?
A. Delaying cloud security reviews or backup strategies exposes businesses to major threats like ransomware, data loss, and system downtime. In 2025, postponing upgrades is no longer strategic—it’s a liability that can disrupt operations, erode client trust, and lead to significant financial loss when, not if, something goes wrong.


Contact CTTS today for IT support and managed services in Austin, TX. Let us handle your IT so you can focus on growing your business. Visit CTTSonline.com or call us at (512) 388-5559 to get started!