Observations and Learnings
Cloud-LLM-Augmented
InfraSec and AppSec
Beyond the Hype, Practical Realities,
Guardrails Sickness, and Cognitive Debt
Ron Michael Khu · Full-Stack AI and DevOps Engineer @ LegalMatch
What this talk is about
Operational truth, not vendor hype.
- The operational reality of using Cloud-LLMs for InfraSec and AppSec work.
- Where AI is a brilliant assistant, and where it is artificially stupid or disobedient.
- Field notes from actual usage. American models (Claude from Anthropic). Open-weight Chinese models (DeepSeek).
- Reality vs the marketing hype of their vendors.
- How to reduce AI flaky behavior by separating deterministic checks from the ones that actually need AI thinking.
- How to manage cognitive debt and intent debt.
Who stays accountable at the end of day. (You do.)
Who this is for
Intermediate builders new or limited in AI adoption.
- Why them. Many experienced teams in big software companies are not as AI-embracing, or as AI-assessing, as other teams are. If that is your team, this is for you.
What the advice is sized for.
- Legacy systems.
- Multi-repository projects.
- Stakes higher than a local school project with no end users.
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.
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.
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.
- If the AI breaks it at 2am, who gets paged? You, or the vendor?
- Why does the newer "frontier" model feel dumber than the one you had last quarter?
- What percentage of your AI-assisted security code have you actually read, line by line?
- If your LLM vendor had a disgruntled insider tomorrow, what would they already know about your infra?
- Could a 5-line bash script do the check you are paying tokens for?
- Who is accountable when the AI confidently writes a wrong IAM policy?
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.
- Field reality: regressions, dumbed-down tool use, over-restrictive refusals.
- Among advanced devs today, Claude is widely considered crippled. DeepSeek is still smarter for a lot of real work, and it is open-weight on top of that.
- Trusting marketing benchmarks leads to fragile pipelines.
Fair disclaimer. Rankings here are a snapshot, not a verdict.
- Can flip. Vendors ship, degrade, and ship again. Re-evaluate per quarter, not per keynote.
- Domain-shaped. Example: Claude builds JavaScript decks and can see its own render. DeepSeek has no vision API and must approximate layout from text alone.
- Takeaway. Match the model to the task. Keep two or three in rotation.
Field test
“Is this site secure?”
Months ago I tried the same prompt across several models.
| Posture | Immediate & 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.
- Examples. Refusing to parse a payload capture. Refusing to help on a log that contains PII you own. Refusing to touch an IAM policy because the prompt says "exploit."
- The hidden cost. Hours bled engineering jailbreaks for benign 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.
| Axis | Deterministic script | Human | LLM |
| Cost | cheap, one-time | expensive, finite | cheap per call, drifts |
| Repeatability | perfect | bounded by fatigue | per-call variance |
| Exposure | none | contained | leaks code and infra outside |
| Accountability | the author | the human | still the human |
| Fails by | logic bug | missed detail | hallucination + confident wrong |
Part 7 · Cognitive debt
Accepting AI code you cannot defend.
- Symptom. Your repo passes checks nobody can defend in a code review.
- Compound interest. Six months later it breaks, and nobody on the team knows why that firewall rule exists.
Fix: AI explains. You understand. Then you ship.
Part 8 · Intent debt
What you meant vs what the AI shipped.
- Example 1. Asked for "block external access to admin." Got a rule that blocks external access, except for a hardcoded CIDR the AI invented.
- Example 2. Asked for "least privilege S3 policy." Got a wildcard permission with a comment that says
// least privilege.
- Silent security gaps. The code reads right. The intent is wrong.
Fix: verify the enforcement, not the vibes.
Part 9 · Field rules
Six rules for the operator.
- 1. Least privilege for AI agents. Treat an LLM service account like a junior contractor from a vendor you cannot audit.
- 2. Deterministic to scripts. Probabilistic to the LLM. Never swap.
- 3. Do not paste prod secrets, topology, or customer data into a cloud LLM. If you must send infra context, send a redacted shape.
- 4. For sensitive work, prefer open-weight models you host. You keep the weights. The data does not leave the box.
- 5. Same code-review bar as a dev's. No "it is just a quick fix" exceptions.
- 6. Verify the intent, not the vibes.
Part 10 · Level yourself, not just your infra
The real cost is the operator who stops learning.
- The real cost of AI-first operation is not tokens.
- Use the LLM as a learning amplifier. Ask it to teach you, not just do.
- Then you can audit it. Then you can disagree with it. Then you are actually accountable.
Build yourself up, not just your output.
Join the communities
Local and global. Participate in the discussions.
- Why it matters. No single operator tracks every model regression, every quiet nerf, every new attack vector. The field moves too fast for one person.
My own.
- AWS User Group Cebu
- PizzaPy
- IoT Cebu
- CeGNULUG (Cebu GNU/Linux Users Group)
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.
- Scripts for the knowable. LLMs for the judgment. Humans for the accountability.
- The vendor is not your friend. The model is not your senior. You are the operator.
- Deterministic by default. Probabilistic by exception. Accountable always.
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.
Ron Michael Khu · Full-Stack AI and DevOps Engineer @ LegalMatch