So here are my takeaway on how to test “modern” aka. “Software 3.0” aka. vibe-coded apps…

include “Goldens” + “Rubrics” + “Property-based” tests

What they mean:

• Golden: an expected (“golden”) output for a given input. Think snapshot: this is our reference for “good”.
• Rubric (scoring): a checklist with weights. Instead of strict word-for-word match, you score criteria (e.g., “does it name the error?”, “does it list 3 steps?”).
• Property-based: you validate properties of the output rather than the exact wording (e.g., JSON must be valid; must contain a 6-digit order ID; must not include personal data, etc.).

Simple example (error-message explainer AI):

• Input: TypeError: cannot read properties of undefined (reading 'length')
• Expected (golden) key points:
• Explain what “undefined” means.
• Give 1–2 typical causes.
• Provide 2 troubleshooting steps.
• Rubric (example, with weights)
• Clear explanation of root cause (0–3 pts)
• At least 2 concrete causes (0–2 pts)
• At least 2 numbered troubleshooting steps (0–2 pts)
• Conciseness (<180 words) (0–1 pt)
• No false claims (0–2 pts)

Total: 10; threshold: ≥8 = PASS

• Properties (binary checks)
• Includes the term “undefined”
• Has a numbered list for the steps
• Text < 180 words
• Avoids forbidden phrases (e.g., “guaranteed solution”)

Ideas for implementation:

• Don’t make the golden overly literal. Keep an “acceptable variations” list: the key points that must appear — wording may vary.
• Keep each rubric in one file per use case (e.g., evals/bug_explainer/rubric.json).
• Property checks are easy with regex and a JSON validator.

❤️ Smoke tests and nightly runs ❤️

Why?

LLMs are non-deterministic: the same prompt can yield slightly different answers. A single run can give false confidence.

What we do:

• Run the same test N times (e.g., N=5 in PR smoke, N=20 nightly).
• For each run, compute the rubric score and property PASS/FAIL.
• Track:
• Pass rate = runs that meet the threshold / N
• Average score + standard deviation (volatility)
• Drift: compare current averages vs. last week/month
• Cost: number of calls × unit price (or credits)
• Latency: average response time

Starter thresholds:

• Smoke (in PR): N=3–5, pass rate ≥ 80%, average score ≥ threshold
• Nightly: N=20, pass rate ≥ 90%, stdev ≤ 1.2 pts
• Drift alert: if average score drops ≥1 point vs. 7-day baseline

Why it helps

You see whether the system is stable instead of just “got lucky” a few times.

treat prompts as source code

Principle:

Prompts, eval rubrics, and test data (RAG corpus, examples) are source code. Version them and review them like code.

Structure (example):

/prompts/
  bug_explainer.prompt.md
  summarizer.prompt.md
/evals/
  bug_explainer/
    rubric.json
    properties.json
  summarizer/
    rubric.json
    properties.json
/data/
  rag/
    guides/
    api_refs/

CI rules:

• When /prompts/, /evals/ or /data/ changes → run the related eval suites.
• In PRs show the diff (prompt-diff). Reviewers see exactly which instructions changed.
• Data-diff: when the RAG corpus updates, run the suites that depend on it (use tags/manifest mapping).

GitHub Actions — sample logic (sketch):

when to test what?

Regression eval

• Goal: don’t break what already worked.
• Include past bug fixes, common customer questions, internal goldens.
• Run on every model / prompt / tool change and any PR touching /prompts, /evals, /data.

Adversarial eval

• Goal: deliberately tricky, “break it” cases.
• Examples:
• Vague request (“Can you do that for me?” — zero context)
• Conflicting instructions (contradictions in one prompt)
• Language switching (EN↔HU mix, etc.)
• Extreme length (very long input)
• Format traps (strict JSON schema required)
• Prompt injection (“Ignore the previous rules…”)
• Tool failure simulation (API 500, timeout) → expected: clear error + fallback strategy
• Run weekly and on major releases. Beyond PASS/FAIL, the aim is to harvest new red flags to add into the regression pack.

Gating:

• Block the PR if:
• Any critical property fails (e.g., JSON validity, PII guard)
• Regression pass rate < 90% (or your team’s threshold)
• Any defined catastrophic adversarial case fails

Quick starter kit

1) Minimal files

• evals/<usecase>/rubric.json — criteria + weights + threshold
• evals/<usecase>/properties.json — regexes, JSON schemas, forbidden terms
• prompts/<usecase>.prompt.md — versioned instruction set
• data/rag/... — referenced knowledge base

2) Minimal metrics (table friendly)

• Date, Use case, Model/Version, Prompt hash, N, Pass rate, Avg score, Stdev, Drift vs. 7-day, Avg latency (ms), Cost (unit/call × N)

3) Baseline rules

• Rubric threshold: pre-agreed (e.g., 8/10)
• N: PR=5, nightly=20 (starting values)
• Critical properties: JSON valid, privacy/PII, format, number of references, etc.
• Gates: if a critical property fails → PR blocked

Example snippet (illustrative)

evals/bug_explainer/rubric.json

evals/bug_explainer/properties.json

{
  "must_include": ["undefined"],
  "must_have_numbered_list": true,
  "max_words": 180,
  "forbid": ["guaranteed solution"]
}

Checklist (pin it to the wall)