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by Sentrygetsentry/skills1k stars
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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.

Use this Skill: https://skilld.dev/gh/getsentry/skills/prompt-optimizer

This session only. Nothing lands on disk.

SKILL.md

≈88 tokens always: the name and description. ≈1.1k when used: this file. ≈8.3k more on demand in 6 files.

Prompt Optimizer

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

Load Only What You Need

Need Read
New prompt references/core-patterns.md, references/model-family-notes.md, references/transformed-examples.md
Existing prompt references/meta-optimization-loop.md, references/core-patterns.md, references/model-family-notes.md
Model-family port references/model-family-notes.md, references/core-patterns.md
Repeated failures references/meta-optimization-loop.md, references/core-patterns.md
Weak or ambiguous draft references/transformed-examples.md
Provenance SOURCES.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 type Examples
Agent rules AGENTS.md, CLAUDE.md
Specs specs/*.md, docs/api.md
Policies SECURITY.md, docs/releasing.md
Examples examples/, 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

Source: SKILL.md on GitHub

No alerts16d3 checks · Risk SAFE
  • Gen Agent Trust Hub16d

    No security issues detected. The skill provides a structured framework for prompt optimization, using patterns to isolate user input and referencing official documentation from trusted technology providers.

  • Socket16d

    No alerts

  • Snyk16d

    Risk: LOW · No issues

Signed by skilld at c190d36. This ties the file your Agent reads to that commit on GitHub. It does not review the instructions.

Last checked against GitHub yesterday.

Activeupdated 5 months ago
  • prompt-engineering
  • prompt-optimization
  • claude
  • openai
  • gemini
  • system-prompts
  • evals
  • agent-prompts
  • llm

README badge

README badge for getsentry/skills/prompt-optimizer

Designs and refines agent prompts through structured evals, inventorying external context, and iterating on prompt layers (system, developer, user) without editing before defining success criteria. Covers porting prompts across OpenAI, Claude, and Gemini model families, debugging repeated failures, and building eval sets to validate changes.

Generated from the current SKILL.md.

Does this skill work with Claude, GPT, and Gemini?
Yes. The skill includes model-family-specific notes and adapters for OpenAI, Claude, and Gemini, and can port prompts between them.
What do I need to provide to start optimizing a prompt?
At minimum: the current prompt, target model family, task type (new/refine/port/debug), success criteria, and failure cases. If success criteria are missing, the skill guides you to build a small eval set first.
Does this skill handle tool-use and schema optimization?
The skill addresses tool-policy wording in prompts and identifies when failures stem from weak tool descriptions or schemas rather than prompt text alone, but delegates schema changes to provider-native tool definitions.
Can I use this skill to debug a prompt that's failing repeatedly?
Yes. The skill includes a meta-optimization loop for clustering failures by root cause, generating candidate rewrites, and comparing them on the same eval cases to find the fix.
Does this skill create evals, or just optimize existing prompts?
It does both. If you lack success criteria or examples, the skill guides you to build a small eval set before optimization begins.

Generated from the current SKILL.md. These answers refresh after source changes.