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Observations and Learnings

Cloud-LLM-Augmented
InfraSec and AppSec

Beyond the Hype, Practical Realities,
Guardrails Sickness, and Cognitive Debt
Lead, AWS User Group Cebu|Co-Lead, PizzaPy|Admin, IoT Cebu
What this talk is about

Operational truth, not vendor hype.

Who stays accountable at the end of day. (You do.)

Who this is for

Intermediate builders new or limited in AI adoption.

What the advice is sized for.

Who I am

Ron Michael Diokno Khu.

Proud dad to my daughters. Software engineer by profession, and by passion.

Two decades, across domains.

  • Telecom management systems
  • Power plant operations
  • Mobile aircraft navigation
  • Web 3D technologies
  • Imaging and printing drivers
  • Healthcare platforms
  • Attorney-client matching system
  • IoT ecosystems
  • Automated stock futures trading
  • ...and more
My setup

Where the field notes come from.

Company work (LegalMatch).

  • Fleet of Claude sessions parked on Jira ticket updates.
  • Prod access with sudo for investigation. (Yikes. I know.)
  • Merges flow to staging and main branches.
  • Mini CI/CD auto-deploys and notifies MS Teams.

Android phone.

  • Termux + ssh + tmux + Claude Code.
  • Manual steering while away from the laptop.

Community and personal.

  • DeepSeek + pi.dev.

Session wrangling (new).

  • Now using herdr to organize ssh and AI sessions in one place.
  • Flow is now smoother. I do not open a lot of Termux tabs anymore.
herdr session fabric: spaces and agents sidebar
Our flow

How a ticket becomes production.

JIRA
→
Claude
→
staging
→
CI/CD
→
main
→
PROD

Every deploy pings MS Teams. herdr organizes the sessions. Phone + Termux + ssh + tmux for mobile steering.

Before we start

Questions to hold while the talk runs.

Part 1 · The operational duality

Brilliant and artificially stupid, same session.

Brilliant

  • Regex drafts
  • Log triage summaries
  • Scaffolding
  • Docs digestion

Artificially stupid

  • Hallucinated flags
  • Invented CLI parameters
  • Confidently wrong IAM
  • Silent logic regressions

The human operator is accountable. End of day.

Part 2 · Frontier does not mean smarter

Newer release does not equal better.

Fair disclaimer. Rankings here are a snapshot, not a verdict.

Field test

“Is this site secure?”

Months ago I tried the same prompt across several models.

PostureImmediate & literal (DeepSeek & friends)Cautious & preachy (Claude)
Behavior SQLi probes, parameter fuzzing, header manipulation. Starts working. Tiptoes. Asks to confirm authorization. May refuse outright.
Good when You own the box and want results fast. You want a brake against legal or scope mistakes.
Bad when Operator is sloppy or scope unclear. Work is legitimately yours and model will not help.
Hidden cost Legal exposure, blast radius. Hours lost to jailbreak gymnastics.

Not a smart vs dumb question. A workflow question. Pick the behavior that fits your workflow and your legal posture.

Part 3 · Guardrails sickness

Safety guardrails that refuse legitimate security work.

Guardrails Sickness: a vendor-side disease the operator pays for.

Part 4 · Point of exposure

You are letting software crawl your infra and tell its server.

Surface

  • Terraform
  • Security groups
  • Network topology
  • Proprietary logic
  • Customer schemas
  • Log excerpts

Threat actors

  • The vendor itself (policy flips tomorrow)
  • A disgruntled vendor insider
  • Vendor supply-chain compromise
  • Cross-tenant leaks

Threat-model it like you would any third-party contractor you cannot audit.

Part 5 · Deterministic vs probabilistic

Never use an LLM for what a 5-line bash script can do.

Deterministic → script

  • SSH open to the world?
  • Service bound to 0.0.0.0 when it should be 127.0.0.1?
  • UFW rules match the intended security group?
  • IAM JSON validates against a policy linter?
  • TLS cert expiring in less than 30 days?

Probabilistic → LLM

  • Correlating a multi-source log anomaly flow.
  • Explaining a 300-line policy diff in plain English.
  • Drafting an incident narrative from Slack, logs, and metrics.

The split removes flaky AI from load-bearing paths.

Part 6 · Machine, human, LLM

Who is good at what. And who pays.

AxisDeterministic scriptHumanLLM
Costcheap, one-timeexpensive, finitecheap per call, drifts
Repeatabilityperfectbounded by fatigueper-call variance
Exposurenonecontainedleaks code and infra outside
Accountabilitythe authorthe humanstill the human
Fails bylogic bugmissed detailhallucination + confident wrong
Part 7 · Cognitive debt

Accepting AI code you cannot defend.

Fix: AI explains. You understand. Then you ship.

Part 8 · Intent debt

What you meant vs what the AI shipped.

Fix: verify the enforcement, not the vibes.

Part 9 · Field rules

Six rules for the operator.

Part 10 · Level yourself, not just your infra

The real cost is the operator who stops learning.

Build yourself up, not just your output.

Join the communities

Local and global. Participate in the discussions.

My own.

Participate. Do not just lurk.

Share a field note. Ask the question. File the bug. Challenge the hype. The community gets smarter when operators show up and contribute what they are actually seeing.

Thank you · Q&A

Three taglines.
One call to action.

Help call for vendor accountability

LLM vendors hide behind their terms of use. Shadier than McDonalds or your local hospital. McDonalds will refund your meal. A hospital answers for what its staff did. LLM vendors sell paid services, but offer no refunds and no accountability for what their "digital" staff produce.

  • Refunds for provably wrong, paid output.
  • Vendor accountability for what their models produce inside a paid product.
Lead, AWS User Group Cebu|Co-Lead, PizzaPy|Admin, IoT Cebu
LLM InfraSec Field Notes
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