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Prompt Optimizer

SentryOfficialPublished by Sentry

  • Skill
  • Workflow
  • Agent tooling
  • Apache-2.0
  • No issues found

From the author

Creates, optimizes, and iteratively refines agent prompts, system prompts, developer prompts, and reusable prompt templates. Use when asked to improve a prompt, optimize a system prompt, rewrite an agent prompt, tune prompt wording, make a prompt more reliable, port prompts between OpenAI, Claude, or Gemini, or build prompt evals.
— the description by Sentry

AutoGineer summary

Written by AutoGineer from the skill’s own files, not by the author

The Prompt Optimizer provides a rigorous, systematic approach to prompt engineering. Rather than relying on intuition, it mandates the creation of evaluation sets (evals) to measure performance, identify failure modes, and validate improvements. The workflow guides users through capturing contract requirements, inventorying external context, choosing model-specific strategies, and executing a disciplined optimization loop. It emphasizes separating stable policy from task-local context and provides a structured method for comparing candidate prompts to ensure changes are causal and effective.

What it does

  • Defines a structured contract for prompt requirements, success criteria, and constraints.
  • Establishes a repeatable optimization loop using evaluation sets to cluster and address failure modes.
  • Provides patterns for layering prompts to separate stable policy from dynamic user input.
  • Offers strategies for porting prompts across different model families like OpenAI, Claude, and Gemini.
  • Maintains an optimization log to track hypotheses, edits, and results to prevent regression.
  • Validates prompt candidates against holdout cases to ensure robustness and prevent overfitting.

When to use it

  • When you need to improve the reliability or performance of an existing agent or system prompt.
  • When porting a prompt between different LLM providers or model versions.
  • When a prompt is failing consistently on specific edge cases or ambiguous inputs.
  • When you need to build a reusable prompt template that maintains consistent behavior across tasks.
  • When you want to move from ad-hoc prompt editing to a data-driven, evidence-based development process.

Advantages

  • Reduces guesswork by grounding all edits in concrete evaluation results.
  • Prevents prompt bloat by enforcing clear separation between policy, examples, and context.
  • Ensures behavioral consistency by using holdout validation to check for regressions.
  • Provides a clear, repeatable framework for team-based prompt development.
  • Helps identify when failures are due to model limitations rather than prompt wording.

Usage examples

“Optimize my customer support agent prompt to reduce hallucinations regarding refund policies.”
The agent will guide you to define success criteria, create a small eval set of refund queries, cluster current failure modes, and iteratively refine the prompt's policy section until performance stabilizes.
“Port this system prompt from GPT-4 to Claude 3.5 Sonnet.”
The agent will analyze the original prompt, identify model-specific dependencies, create a portable base, and generate adapter notes to ensure consistent behavior on the new model family.

Install

  1. Download the skill as a ZIP:

    https://autogineer.com/agent-skills/getsentry/prompt-optimizer/download
  2. Unzip it into the cross-client skills folder of your project:

    mkdir -p .agents/skills && unzip prompt-optimizer.zip -d .agents/skills

Documentation by Sentry

Prompt Optimizer

Optimize prompts with evals. Keep every instruction, example, and external context reference causal.

Load Only What You Need

NeedRead
New promptreferences/core-patterns.md, references/model-family-notes.md, references/transformed-examples.md
Existing promptreferences/meta-optimization-loop.md, references/core-patterns.md, references/model-family-notes.md
Model-family portreferences/model-family-notes.md, references/core-patterns.md
Repeated failuresreferences/meta-optimization-loop.md, references/core-patterns.md
Weak or ambiguous draftreferences/transformed-examples.md
ProvenanceSOURCES.md

Step 1: Capture Contract

Record before editing:

  • task type: new, refine, port, or debug

  • target model family and snapshot, if known

  • prompt surface: system, developer, user, tool descriptions, examples, schemas

  • layer owners: platform, deployer/persona, retrieved context, user payload

  • objective and non-goals

  • inputs, tools, and external files available

  • required output shape

  • success criteria and failure cases

  • hard constraints: latency, verbosity, safety, budget, tool use, style

If success criteria or examples are missing, create a small eval set first. If the bottleneck is model choice, retrieval, tool schema, or missing evals, say so before rewriting.

Step 2: Inventory External Context

For repo or agent prompts, list stable context by exact path:

Context typeExamples
Agent rulesAGENTS.md, CLAUDE.md
Specsspecs/*.md, docs/api.md
PoliciesSECURITY.md, docs/releasing.md
Examplesexamples/, tests/fixtures/

Rules:

  • Reference stable files by repo-relative path instead of copying them.

  • Paste only excerpts needed for the prompt or eval case.

  • Mark whether a file is loaded, referenced, or out of scope.

  • Avoid vague context pointers such as "read the docs".

Step 3: Choose Model Strategy

Read references/model-family-notes.md.

  • Known family: optimize for that family.

  • Unknown family: write a portable base plus short adapter notes.

  • Snapshot changes: rerun evals.

  • Cross-family divergence: specialize only the failing layer.

Step 4: Shape Prompt

Read references/core-patterns.md.

  • Put stable policy in system or developer.

  • Put task-local facts, retrieved context, and variables in user-facing sections.

  • Keep one owner per behavior rule.

  • Use headings or tags only to separate content types.

  • Put tool policy in prompt text; keep schemas in provider-native tools.

  • Keep persona light unless it changes behavior.

  • Use the shortest wording that preserves the constraint.

  • Cut filler, repeated reminders, dead examples, and rationale that does not affect evals.

Step 5: Optimize

Read references/meta-optimization-loop.md for refinements.

  1. Baseline the current prompt on the same eval slice.

  2. Cluster failures by root cause.

  3. Write concrete edit criticisms.

  4. Generate two to four candidates:

    • minimal-diff repair

    • structure-first rewrite

    • examples-first or tool-rule variant

    • provider adapter when needed

  5. Compare candidates on the same cases.

  6. Keep a short optimization log.

  7. Validate the winner on holdout cases.

  8. Stop on plateau, oscillation, overfit, excessive cost, or non-prompt bottleneck.

Step 6: Return Package

Return:

  1. Target

  2. Success Criteria

  3. External Context

  4. Optimized Prompt

  5. Adapter Notes

  6. Eval Set

  7. Optimization Log

  8. Residual Risks

For existing prompts, include a concise diff-style note of the main behavioral changes.

Failure Modes

  • editing before defining the eval target

  • mixing policy, examples, and raw context without boundaries

  • duplicating rules across layers

  • putting durable policy in user payloads

  • asking for chain-of-thought

  • keeping contradictory legacy instructions

  • overfitting to one or two examples

  • retaining examples that no longer improve evals

  • fixing tool-use failures only in prompt text when tool descriptions or schemas are weak

  • adding markup that does not reduce ambiguity

  • using persona as a substitute for behavior rules

Files

SPEC.md

Prompt Optimizer Specification

Intent

prompt-optimizer improves reusable prompts through a contract-first, eval-backed workflow.

It should produce shorter, more reliable prompt packages with explicit model strategy, external context inventory, eval evidence, and residual risks.

Scope

In scope:

  • New agent, system, developer, and reusable prompt templates.

  • Refining existing prompts from failures or examples.

  • Porting prompts across OpenAI, Claude, Gemini, or unknown model families.

  • Prompt eval set design, candidate comparison, and holdout checks.

  • Layering stable policy, task-local context, examples, tool policy, and external file references.

Out of scope:

  • Choosing model architecture or fine-tuning strategy except to flag when prompting is not the bottleneck.

  • Rewriting product docs, specs, or policies referenced by a prompt.

  • Creating reusable agent skills.

  • Debugging repository code unrelated to prompt behavior.

  • Asking models to reveal hidden reasoning or chain-of-thought.

Users And Trigger Context

  • Primary users: engineers and agents maintaining prompts for coding agents, product agents, eval harnesses, and model integrations.

  • Should trigger for: improve a prompt, optimize a system prompt, rewrite an agent prompt, tune prompt wording, make prompts reliable, port prompts across model families, build prompt evals.

  • Should not trigger for: normal code review, PR writing, skill authoring, generic documentation editing, or parameter-only tuning.

Runtime Contract

  • Capture the prompt contract before edits: target model, prompt surfaces, layer owners, objective, non-goals, inputs, tools, output shape, success criteria, failures, and hard constraints.

  • Build or request a small eval set when success criteria or examples are missing.

  • Inventory stable external context by exact repo-relative path.

  • Reference docs/specs/policies by path; paste only necessary excerpts.

  • Keep one authoritative owner per behavior rule.

  • Compare candidates on the same eval slice.

  • Validate the selected prompt on holdout cases.

  • Return a reusable package with target, success criteria, external context, optimized prompt, adapter notes, eval set, optimization log, and residual risks.

Source And Evidence Model

Authoritative sources:

  • Local prompt-optimizer runtime files and references.

  • Repository instructions and skill-writer authoring rules.

  • Official OpenAI, Anthropic, and Gemini prompting and eval guidance.

  • Prompt optimization research and framework docs already captured in SOURCES.md.

Useful improvement sources:

  • positive examples: prompts that meet eval targets with fewer tokens and cleaner layering

  • negative examples: prompts with duplicated policy, vague context, stale examples, or weak tool rules

  • eval outputs: failure clusters, holdout regressions, candidate scores, and optimization logs

  • model changes: provider docs or release notes showing changed behavior, tool APIs, or reasoning defaults

Do not store secrets, customer data, private policy text, or long copyrighted prompt/source excerpts in examples.

Reference Architecture

  • SKILL.md contains the runtime workflow and output contract.

  • SPEC.md contains this maintenance contract.

  • SOURCES.md stores source inventory, decisions, coverage, gaps, and changelog.

  • references/core-patterns.md covers prompt structure, layering, markers, external files, tool policy, and symptom fixes.

  • references/meta-optimization-loop.md covers eval-backed iteration.

  • references/model-family-notes.md covers provider adapters.

  • references/transformed-examples.md contains compact examples for new prompts, repairs, and anti-pattern correction.

  • scripts/ and assets/ are unused unless prompt scoring automation or reusable templates become necessary.

Evaluation

  • Lightweight validation: run representative prompt tasks through the contract checklist and verify the package includes external context, eval cases, and residual risks.

  • Candidate validation: compare all candidates on the same working slice and at least one holdout case.

  • Trigger QA: confirm prompt optimization requests trigger this skill while skill writing, code review, and parameter-only tuning do not.

  • Acceptance gates: prompt is shorter or behaviorally justified, rules have one owner, external files are exact, examples are causal, and residual risks name non-prompt bottlenecks.

Known Limitations

  • Prompt behavior can change across model snapshots; the skill must recommend re-running evals after model changes.

  • The skill cannot prove prompt quality without representative eval cases.

  • External files referenced by path are useful only when the runtime agent can access them.

  • Provider-specific advice can drift; refresh official docs when model or API behavior matters.

Maintenance Notes

  • Update SKILL.md when runtime workflow, output package, or failure modes change.

  • Update SPEC.md when scope, evidence policy, evaluation, or reference architecture changes.

  • Update SOURCES.md when source inventory, decisions, coverage, gaps, or changelog entries change.

  • Keep reference files focused; split any file that mixes unrelated lookup needs.

Requirements and compatibility

Works with: Claude Code, Claude apps, OpenAI Codex, GitHub Copilot, Cursor, Gemini CLI, Kiro, OpenCode, Goose, Amp, Roo Code, JetBrains Junie, Factory Droid, Devin (ex-Windsurf), Mistral Vibe, OpenHands, Letta

“Works with” means the tool reads the open Agent Skills format; a skill written for one tool may use features others lack.

Security

No issues found by our static scan· No issues found

A static scan is not a guarantee. Skills are third-party content: review a skill before you let an agent use it.

Attribution and licence

Published by
Sentry
Publisher
Sentry (Official)
Source
getsentry/skills · skills/prompt-optimizer · commit e94f222
Licence
Apache License 2.0 (redistribution allowed)
  • LICENSE (added by AutoGineer from LICENSE)
  • ATTRIBUTION.md (written by AutoGineer)
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