Discussion on The Costliest Cybersecurity Mistakes Companies Still Make and how to fix them Featuring insights from Junior Gilpin, Senior Cybersecurity Engineer, 800 TECH on the radio programme the Digital World.
Cybersecurity today is no longer a “technology issue.” It is a business survival discipline, one that sits squarely at the intersection of reputation, revenue, compliance, and continuity. Yet across industries, the same avoidable mistakes continue to show up in post incident reviews and audit findings. The result is predictable: unnecessary exposure, preventable downtime, and breaches that cost far more than the controls that would have stopped them.
As Junior Gilpin, Senior Cybersecurity Engineer at 800 TECH, puts it plainly: “Compliance isn’t optional anymore; there are legal and financial consequences for getting this wrong.” The modern threat landscape, accelerated by AI, always on commerce, remote work, and expanding data regulations, requires that organizations move from reactive security to deliberate, tested, business, aligned resilience.
Below are the most expensive mistakes companies still make, why they matter now, and what high, performing organizations do differently.
1) Cybersecurity Mistake: Not regularly testing systems, policies, or incident response plans
A policy that isn’t tested is a policy you can’t trust. Too many organizations invest in controls, write procedures, and then assume they will work under stress. That’s a dangerous gamble.
Why this matters now
AI driven attacks, digital supply chains, and nonstop data movement mean risk lives everywhere, across endpoints, cloud platforms, vendors, and human workflows. With that comes legal responsibility through data protection laws and sovereignty rules, as well as severe commercial risk.
Junior’s warning is direct: “Comfort over compliance is why many firms get burnt.” Security that feels good but isn’t validated is not security, it’s optimism.
What good looks like
- Test backups, restores, and failover, not just backup completion reports.
- Run tabletop simulations for real world incident scenarios (ransomware, insider misuse, cloud compromise).
- Review and retest controls after any major system change.
- Treat drills as training, not theatre.
2) Cybersecurity Mistake: Treating disaster recovery as an afterthought
In the Caribbean, disruption is not hypothetical. Floods, earthquakes, and hurricanes are part of the regional operating reality. Yet many firms still approach disaster recovery reactively building plans after a near miss.
Disaster preparedness isn’t optional; it’s survival.
What to do now
- Relocate mission critical infrastructure above known flood lines well before storm season.
- Power down and waterproof vulnerable equipment using covers, bagging, and sealing procedures.
- Prewrite shutdown and restart runbooks so recovery isn’t improvised.
- Test seasonal readiness especially backups and recovery procedures.
Junior shares a practical example: “We moved an entire data centre to the second floor before a storm. When floodwaters came, operations were ready to resume.”
The lesson is simple: resilience pays for itself the first time you need it.
3) Cybersecurity Mistakes continued: Treating data protection as a compliance checkbox
Data protection is now a core business risk lens. With sovereignty rules expanding and privacy regulations tightening, storing sensitive data “anywhere” is no longer acceptable.
What high maturity teams do
- Map where data lives systems, countries, vendors, and shadow IT.
- Minimize exposure by disabling unnecessary collection and retention.
- Align storage and processing with applicable laws and frameworks (GDPR, HIPAA, ISO/IEC 27001, and local regulations).
If you cannot clearly explain where your sensitive data resides and why, you do not control your risk.
4) Cybersecurity Mistake: Avoiding audits because they feel expensive or uncomfortable
Audits are often treated as policing. In reality, they are quality control for one of your most critical business functions: trust. Avoiding audits doesn’t remove risk, it hides it until it becomes an incident.
A practical cadence
- Smaller organizations: semi-annual audits (midyear and year end are high value windows).
- Larger organizations: continuous auditing, because policies and software change too quickly for periodic checks.
A breach that “surprises” you is usually one you didn’t want to look for.
5) Cybersecurity Mistake: Allowing outdated software to linger
Outdated software is the easiest door to leave open. Attackers increasingly “live off the land,” abusing trusted tools and known vulnerabilities rather than deploying obvious malware.
Fix it with discipline
- Enforce automated patching with clear maintenance windows.
- Track end of life systems and schedule upgrades early.
- Monitor internet exposed services for known vulnerabilities.
- Treat “one old box” as a whole network risk, because it is.
6) Cybersecurity Mistakes continued: Underestimating password and MFA hygiene
Weak or reused passwords collapse under modern cracking methods, now turbocharged by GPUs and AI. This is the most preventable foothold attackers get.
Win today
- Use long passphrases (two to four unrelated words).
- Keep substitutions minimal, length beats complexity tricks.
- Enable MFA everywhere, favouring apps or hardware tokens over SMS.
- Use password managers to keep credentials unique and strong.
Simple changes here deliver outsized risk reduction.
7) Cybersecurity Mistake: Not having an incident response plan that’s actually usable
When something feels “off,” minutes matter. Many firms lose time not because they lack tools, but because they lack clarity on who decides what, when.
Be ready before you need to be
- A one-page incident response plan: roles, escalation path, authority to isolate systems.
- A trusted partner on speed dial (MSP/IR team) and the national CSIRT/TTCERT.
- A clean communication alternative if email is impacted.
- A decision matrix for isolating segments without collapsing operations.
Incidents are chaotic. Your plan must reduce chaos, not add to it.
8) Cybersecurity Mistake: Bolting security onto e-commerce instead of designing it in
Online payments are growing fast across the region, and so are attacks targeting weak payment flows and misconfigurations. The right stance is security by design, not security by apology.
Baseline moves
- Use reputable gateways with fraud controls and multicurrency capability.
- Have professional security hardening on auth, sessions, and admin access.
- Run continuous vulnerability scanning plus storefront WAF rules.
- Handle payment data in a PCI, DSS, aligned way, or outsource handling entirely.
Your storefront is not “just a website.” It is a revenue engine and a risk surface.
9) Cybersecurity Mistakes continued: Ignoring physical security
Security doesn’t stop at the login screen. Doors, racks, cameras, visitors, and environmental controls are all part of information security.
Check the basics
- 24/7 camera coverage for entrances, server rooms, and racks.
- Visitor logging and regular badge audits.
- Cable/port exposure in public or semi-public areas.
- Site specific environmental risks (flood, seismic, heat).
Breaches often start with a person walking in, not a hacker logging in.
The Regional Outlook: momentum is real
The Caribbean has made tangible progress through professional communities, stronger industry collaboration, and growing awareness. The gap hasn’t fully closed, but the trajectory is positive. If urgency stays high, a meaningful closing of the region’s cybersecurity maturity gap within the next two to three years is realistic.
Progress doesn’t have to be perfect to be powerful. The costliest Cybersecurity Mistakes we have seen were not sophisticated inevitabilities, they were slow, moving risks that a basic audit, a tested backup, or a patched system would have caught in time.
Slow progress beats no progress. Consistent execution beats reactive panic.
Ready to act? We can help.
800 TECH delivers assessments, remediation roadmaps, and hands on improvements across infrastructure, cloud, users, and physical security tailored to Caribbean realities and regulations. If you’re ready to move from exposure to resilience, we’re ready to partner with you.
