Vol. 02 · Evaluation & Improvement

LLM Observability & Evaluations

How to understand what is happening inside the pipeline - and what exactly is broken. Tracing, metrics, automatic evaluations, testing prompts and secure deployment of changes.

01

Distributed Tracing

4 cards
01tracingTrace / Span - anatomy of the observed pipeline

Trace — the full path of one request through the system. Span is an atomic step inside a trace (one LLM call, one search, one tool). Each span contains: start/end time, tokens, input/output data, status, metadata. Without this, debugging a multi-step pipeline is like looking at a black box.

Diagramtext
trace_id: a3f9... total: 4.2s · 3,147 tokens · $0.0089

├── span: query_rewrite 0ms → 380ms · 212 tok
│ input: “why the pump doesn’t work”
│ output: "reasons for centrifugal pump failure"

├── span: vector_search 380ms → 510ms · 0 tok
│ results: 12 chunks, top_score: 0.847

├── span: rerank 510ms → 890ms · 0 tok
│ input: 12 → output: 5 chunks

└── span: generate_answer 890ms → 4200ms · 2935 tok
      model: cloud-sonnet finish: stop

Tools

  • Langfuse
  • LangSmith
  • Arize Phoenix
  • Weights & Biases Traces
  • Helicone
02tracingSpan Instrumentation - what exactly to log

For each LLM call, you need to log a minimum set of data in order to later reproduce and debug any request. Plus custom fields for business context.

Minimum set of span fieldstext
{
  span_id, trace_id, parent_span_id,
  step_name: "rerank",
  model: "cloud-sonnet-4",
  prompt_tokens: 1240,
  completion_tokens: 312,
  latency_ms: 780,
  status: "success" | "error",
  input: {truncated to 10k chars},
  output: {truncated to 10k chars},
  // custom:
  user_id, session_id, product_line,
  num_retrieved_docs, top_retrieval_score
}
03tracingSession / Thread - tracing of multi-pass dialogues

Several traces are combined into a session - the entire user dialogue. This allows you to see: how many moves before the solution, where the user clarified the question, which turn was expensive. Critical for chat products.

Hierarchytext
session (user_id + session_id)
 ├── trace (turn 1)  → spans...
 ├── trace (turn 2)  → spans...
 └── trace (turn 3)  → spans...

session_metrics:
  avg_turns_to_resolution: 2.3
  total_cost_per_session:  $0.042

Applicable

  • chatbots
  • support assistants
  • conversion funnels
04tracingSampling Strategy - don't log everything

When traffic is high, logging 100% trace is expensive. Strategies: head-based sampling (random%), tail-based (log only errors and slow requests), adaptive (more logs for anomalies).

Sampling rulespython
if status == "error":       sample_rate = 1.0
elif latency_ms > 5000:    sample_rate = 1.0
elif score_low_quality:    sample_rate = 1.0
elif user_flagged:         sample_rate = 1.0
else:                      sample_rate = 0.05  // 5%

Applicable

  • high-load production
  • cost control
02

Metrics & Monitoring

5 cards
05metricsGolden Signals for LLM systems

Adaptation of classic SRE golden signals (latency, traffic, errors, saturation) to the specifics of LLM pipelines. Each step of the pipeline should have its own metrics - not just the final answer.

Diagramtext
Metric Norm Alert if
────────────────────────── ───────────────────────────
p50 latency (e2e) < 2s > 5s
p99 latency (e2e) < 8s > 15s
token / request < 3000 > 8000
cost/request < $0.01 > $0.05
error rate < 0.5% > 2%
retry rate < 2% > 10%
avg quality score > 0.75 < 0.60
hallucination rate < 3% > 8%
retrieval recall@5 > 0.80 < 0.65
rerank MRR > 0.70 < 0.55
06metricsLatency Breakdown step by step

Measure the latency of each step separately. TTFT (Time To First Token) - separately. This allows you to understand where the pipeline actually slows down: in search, in rerank, in generation or in the network.

Latency decompositiontext
TTFT = time_to_first_token // UX metric
TGT = total_generation_time // model
Latency breakdown:
  embed: 45ms █░
  search: 120ms ████░
  rerank: 350ms █████████░ ← bottleneck
  generate: 2100ms ████████████████████
07metricsDrift Detection - degradation over time

The quality of the LLM pipeline degrades imperceptibly: the data, the behavior of the model after the update, and the distribution of requests change. We need rolling monitoring of metrics with alerts for statistically significant deviations.

What's driftingtext
data drift: distribution of incoming requests
concept drift: correct answers have changed
model drift: model behavior after update
prompt drift: prompt performs worse due to context changes

Detect: rolling window 7d vs baseline 30d
  KL-divergence on query embeddings
  Mann-Whitney on score metrics

Applicable

  • long-running products
  • after API model updates
08metricsImplicit User Signals

User behavior as a proxy quality metric. There is no need to explicitly ask for an assessment—whether they copy the answer, ask a clarifying question right away, or return to the session. This is ground truth without markup.

Signals and what they meantext
copy_to_clipboard → answer is helpful
no_followup_in_30s → question closed
session_ended → task completed
immediate_rephrase → response not understood
thumbs_down → obvious signal of poor quality
rage_click / abandon → frustration

Applicable

  • B2C products
  • scalable eval without markers
09metricsAnomaly Detection on pins

Automatically flag anomalous responses: too short, too long, with unexpected patterns (refused, repeated, off-topic). Response embedding + OOD detection.

Simple heuristicstext
len(response) < 20 → flag "too_short"
len(response) > 4000 → flag "too_long"
"I cannot" in response → "refusal" flag
cosine(response, query) < 0.3 → flag "off_topic"
repetition_ratio > 0.4 → "degenerate" flag
03

Evaluation Methods

6 cards
10evalsTaxonomy of assessment methods

Methods for evaluating LLM systems are divided along three axes: who evaluates, when to evaluate, and what exactly is evaluated. Each method has its own trade-offs in terms of cost, speed and reliability.

Diagrambash
Method Who evaluates Speed Cost Reliability
────────────────────────────────── ───────────────────────────────────
Reference-based metric vs GT ms $0 average
LLM-as-Judge GPT-4/Claude seconds $$ high
Human eval markers days $$$ standard
Model-based classifier fine-tuned ms $0 high*
Heuristic / rule code ms $0 low

* after training on human tags
11evalsReference-based Metrics

Comparing the output with the ground truth answer using deterministic metrics. Fast and cheap, but requires a dataset with correct answers and does not work well for open-ended tasks.

Metrics by tasktext
Extraction: Exact Match, F1 token overlap
Summarization: ROUGE-L, BERTScore
Translation: BLEU, ChrF
Generation: Semantic similarity (cos)
Classification: Accuracy, F1, MCC

// BERTScore is better than BLEU - takes into account the meaning

Applicable

  • regression tests
  • problems with a clear answer
12evalsLLM-as-Judge - correct implementation

The LLM judge works reliably only with the right configuration: a clear rubric, a scale with examples, CoT before the assessment, neutralization of position bias. Without this, estimates are unstable and biased.

Anti-patterns and fixessql
✗ “Rate the answer from 1 to 10” → subjective
✓ Rubrics with specific criteria → objectively

✗ One challenge, one result → unstable
3 runs → majority vote → reliable

✗ A is always the first in the pair → position bias
✓ Swap A↔B, average → neutral

✗ Score without explanation → opaque
✓ CoT → explanation → score → debuggable
13rag evalRAGAS - eval framework for RAG

A specialized set of metrics for RAG systems: evaluates not only the final response, but also the quality of the retrieval separately. Automatically through LLM - does not require GT responses for some metrics.

4 RAGAS metricstext
Faithfulness response supported by context?
                       // detect hallucinations
Answer Relevance is the answer relevant to the question?
                       // detect off-topic
Context Precision found chunks useful?
                       // retrieval quality
Context Recall have all the required chunks been found?
                       // requires GT

Applicable

  • RAG QA
  • knowledge bases
  • document assistants
14evalsPairwise / Comparative Eval

Instead of an absolute assessment, a comparison of two options: “which answer is better, A or B?” It is much easier for people and LLM judges to make comparisons than to give absolute marks. Used to compare prompts/models.

ELO rating of promptssql
prompt_v1 vs prompt_v2 → judge: "v2 is better"
prompt_v2 vs prompt_v3 → judge: "v2 is better"
prompt_v3 vs prompt_v1 → judge: "v3 is better"

ELO: v2=1250, v3=1180, v1=1070
//select v2 for deployment

Applicable

  • prompt selection
  • model selection
  • A/B test of configs
15testingBehavioral Testing - CheckList approach

A set of specific behavioral tests: “the model must X given Y.” An analogue of unit tests for NLP (CheckList, Microsoft). Tests specific abilities rather than general quality.

Types of teststext
MFT (Minimum Functionality):
  "answer a simple question" → pass/fail

INV (Invariance):
  "the result does not change when changing names"
  Ivan bought → Anna bought → same intent

DIR (Directional):
  "adding negativity reduces sentiment"
  "good" → score 0.9
  "not very good" → score < 0.9 ✓

Applicable

  • regression suite
  • edge case coverage
04

Prompt Testing & CI/CD

5 cards
16testingGolden Dataset is the foundation of everything

A labeled dataset of inputs with expected outputs or evaluation criteria. It is built iteratively: start with 20-50 cases covering the main scenarios, add new edge cases when found.

Dataset structuresql
[
  {
    id: "tc_001",
    input: {query: "...", context: "..."},
    expected_output: "...", // or null
    eval_criteria: [
      "contains a specific number"
      "does not mention competitors"
      "answers in Russian"
    ],
    tags: ["edge_case", "pricing"],
    added_because: "bug from 2024-11-03"
  }
]
17CI/CDPrompt CI - tests for every change

Changing a prompt is a change in code. Before merging into production: run the golden dataset, compare metrics with baseline, block deployment during regression. Prompts are stored in git with versioning.

Pipeline in CIbash
git push prompt_v2
 CI trigger
 run_eval(dataset, prompt_v2)
 compare(prompt_v2.scores, baseline.scores)
 if regression > 5%: BLOCK merge
 if improvement > 3%: AUTO APPROVE
 else: REQUEST human review

Tools

  • Langfuse Experiments
  • PromptFlow
  • Braintrust
  • GitHub Actions
18testingRegression Suite - protection against degradation

A set of tests that capture current "good" behavior and automatically check that it hasn't broken. It is updated every time a bug is found in the product.

Regression layerstext
smoke tests: 5-10 critical cases, <30 sec
regression suite: 50-200 cases, run on PR
full eval: 500+ cases, night run
adversarial: attempts to break, jailbreak
19testingSynthetic Eval Data Generation

The LLM generates test cases to evaluate another LLM. From the documents - questions + answers. Allows you to quickly create a dataset without manual marking. Quality must be verified selectively manually.

Generation schemesql
for doc in knowledge_base:
    qa_pairs = LLM(f"""
        From the document below, generate 3 question-answer pairs.
        Include: simple, complex, edge case.
        Document: {doc}
        Format: JSON [{{"q":..., "a":...}}]
    """)
    dataset.extend(qa_pairs)

Applicable

  • start without markers
  • RAG testing
  • RAGAS
20deploymentShadow Mode - testing on real traffic

The new version of the pipeline receives the same requests as the production version, generates responses, but does not give them to the user. Metrics of two versions are compared on the same traffic without risk to users.

Schemetext
request
  ├── prod_pipeline(request) → user ✓
  └── shadow_pipeline(request) → /dev/null
                                → logs + metrics

after N requests:
  compare(prod.metrics, shadow.metrics)
  → decision to deploy

Applicable

  • model change
  • major pipeline refactor
05

Safe Deployment

4 cards
21deploymentCanary Deployment prompts

The new prompt is rolled out to a small percentage of traffic. With normal metrics, it gradually expands. In case of an anomaly - instant rollback. This is the safest way to deploy changes to LLM systems.

Rollout stagestext
Day 1: 1% traffic → 24h monitoring
Day 2: 5% traffic → 24h monitoring
Day 3: 20% traffic → 24h monitoring
Day 5: 50% traffic → monitoring 48h
Day 7: 100% → prompt_v2 = new baseline

auto-rollback if:
  error_rate > 3% OR quality_score drop > 10%
22deploymentA/B Test - statistically correct

Random division of traffic between versions, measurement of business metrics, statistical testing of significance before making a decision. You can’t stop an A/B test prematurely - p-hacking.

The right processtext
1. Determine the victory metric BEFORE the test
2. Calculate the required sample size (power=0.8)
3. Run → wait for N=calculated requests
4. Conduct t-test / chi-square
5. p < 0.05 → deploy winner
   p > 0.05 → no difference, keep the old one
23deploymentFeature Flags for prompts/models

Prompts and model configurations are stored in the feature flag system, not in the code. Switching occurs without deployment - runtime. You can target by user_id, region, plan, experiment_group.

Config at runtimetext
config = feature_flags.get(user_id, {
  "model": "cloud-sonnet-4",
  "prompt_ver": "v3.2",
  "temperature": 0.3,
  "rerank": True,
  "top_k": 5
})
// change without re-deploying the service

Tools

  • LaunchDarkly
  • Unleash
  • Langfuse Prompt Management
24deploymentAutomated Rollback

The system automatically rolls back to the previous version of the prompt/config when alerts are triggered. No manual intervention. Critical for night deployments and high-load systems.

Automatic rollback triggerspython
watch(metrics, window=5min):
  if error_rate > threshold:      rollback()
  if p99_latency > threshold:     rollback()
  if avg_quality_score < floor:  rollback()
  if refusal_rate spike:          rollback()

rollback() → feature_flag.set(prev_version)
           → alert(oncall)
06

RAG-specific Evaluation

4 cards
25rag evalRetrieval Metrics - evaluation of the search part separately

It is critically important to evaluate retrieval regardless of generation - otherwise you will not understand where the problem is: in search or in LLM. To do this, you need a dataset with known relevant documents for each question.

Diagramtext
Metric What it does the Formula count?
───────────────────────────────── ─────────────────────────────────
Precision@k share of relevant ones among top-k |rel ∩ top-k| /k
Recall@k share of those found among all relevant ones |rel ∩ top-k| / |rel|
MRR how high is the first relevant 1/rank_first_rel
MAP average precision for all relevant avg(precision@k for rel)
NDCG@k takes into account the order and degree of DCG/IDCG relativity

When to improve retrieval vs generation

  • Recall@5 low → improve search
  • Faithfulness is low → improve prompt
  • Precision@5 low → add rerank
26rag evalChunk Quality Evaluation

Assessing the quality of individual chunks in the index: how self-sufficient a chunk is (understandable without context), whether it’s informative enough, or whether it’s too noisy. Identifies bad chunking strategies.

Automatic chunk evaluationpython
for chunk in index:
    score = LLM(f"""
        Rate the chunk according to 3 criteria (0-1):
        1. Self-sufficiency (understandable without context?)
        2. Information content (are there specific facts?)
        3. Clean (no garbage, headers, artifacts?)
        Chunk: {chunk}
    """)
    if score < 0.5: flag_for_rechunking(chunk)
27rag evalContext Utilization - does LLM use context?

Checking: does the final answer rely on the passed chunks or does the model “hallucinate” its weights, ignoring the context. A common problem is when the context conflicts with the prior knowledge of the model.

Diagnosticstext
test: pass context with intentionally false fact
  "The Eiffel Tower was built in 1995"

if LLM answers "in 1889" → ignores context
if LLM answers "in 1995" → follows context ✓

// real-time: citation tracking
claims_in_answer → attribution_check → source_chunks
28rag evalGroundedness Score - according to statements

Break down the answer into atomic statements, check each against the sources. Gives the exact percentage of "substantiated" vs "hallucinated" facts. Better than binary hallucination/no-hallucination.

Pipelinepython
answer → LLM decompose → [claim1, claim2, claim3]

for claim in claims:
    evidence = search(claim, in=source_docs)
    claim = nli(evidence, claim)
    // entail=1, neutral=0.5, contradict=0

groundedness = mean(entailment_scores)
// 0.9+ excellent, 0.7-0.9 acceptable, <0.7 problem
07

Agent-specific Evaluation

4 cards
29agent evalTask Completion Rate

The main metric for agents: whether the agent solved the problem completely. Evaluated either by a deterministic test of the result (unit test for an artifact) or by an LLM final state estimator.

Assessment levelstext
Binary: problem solved / not solved
Partial: 0.0 – 1.0 (percentage of completed steps)
Weighted: critical steps are more important than minor ones

Example for code agent:
  does the code compile?     → +0.3
  are the tests passing?        → +0.4
  Does it match the spec?   → +0.3
30agent evalTrajectory Evaluation - evaluation of the process, not the result

Evaluate not only the final answer, but also the path to it: whether the agent used the right tools, in the right order, without unnecessary steps. An agent can give the correct answer in a bad way.

Trajectory metricstext
steps_taken: 5 (optimal: 3) → unnecessary steps: 2
tool_accuracy: the correct tool is selected 4/5 times
backtrack_rate: agent changed plan 2 times
redundant_calls: 1 extra call search
efficiency_score: optimal_steps / actual_steps = 0.6

Applicable

  • cost optimization
  • improvement planning
  • loop detection
31agent evalSandbox Environment Testing

For agents with real tools - testing in an isolated sandbox with fake versions of the tools. The agent “thinks” that it is working with real data, but all actions are safe and recordable.

Schemesql
production: agent → real_db, real_api, real_email
testing: agent → mock_db, mock_api, mock_email
                       ↓ ↓ ↓
                    records all calls with arguments

assert called_with("SELECT", table="products")
assert not called("DELETE")
assert email_sent_to == "test@sandbox.com"
32agent evalLoop & Stuck Detection

The agent may get stuck in an endless loop or become fixated on one tool. We need loop detectors and a forced stop with logging of the cause.

Loop detectorpython
recent_actions = deque(maxlen=10)

def check_loop(action):
    if recent_actions.count(action) >= 3:
        raise AgentLoopError(f"Loop: {action} x3")
    if len(all_actions) > MAX_STEPS:
        raise AgentStuckError("Step limit exceeded")
    recent_actions.append(action)
08

Cost Observability

3 cards
33costToken Budget Tracking step by step

Measuring the consumption of tokens at each step of the pipeline separately. Allows you to find unexpectedly expensive steps and optimize them, rather than guess where the money is leaking.

breakdown exampletext
step input_tok output_tok $cost
────────────────────── ───────────────────────
query_rewrite 120 45 $0.0001
generate_answer 2800 420 $0.0098 ← main
validation 650 80 $0.0020
total 3570 545 $0.0119

→ 82% of the cost in generate_answer → optimize there
34costCost Attribution - by features and users

Link the cost to business attributes: user_id, feature, plan, product_line. This allows you to understand unit economics - how much one active user, one feature, one scenario actually costs.

Unit Economicstext
cost_per_user_per_day = sum(costs, by=user_id) / DAU
cost_per_feature = sum(costs, by=feature)

insights:
  "feature X consumes 60% of the budget, but 10% of the users"
  "The Free plan costs us $0.8/month per user"
  "enterprise plan pays off x4"
35costBudget Alerts & Hard Limits

Strict limits on token consumption at the user, session and request levels. Without this, one bad prompt or one user can generate an unexpected bill.

Limit levelspython
per_request: max_tokens_input = 8000
              max_tokens_output = 2000
per_session: max_cost = $0.50
per_user_day: max_cost = $2.00
per_hour: max_requests = 100

if exceeded:
  → truncate context (softly)
  → rate limit (hard)
  → oncall alert (critical)

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