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getsentry/prompt-optimizer

getsentry

prompt-optimizer

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.

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New~1.1k
v1.0Saved Jul 11, 2026

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
Files7
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Overall Score

89/100

Grade

A

Excellent

Safety

92

Quality

88

Clarity

92

Completeness

84

Summary

A disciplined prompt-optimization workflow that guides agents through contract-first prompt engineering with eval-backed iteration. The skill structures prompt creation and refinement as a systematic process: capture success criteria and external context, baseline prompts on representative cases, cluster failures, generate candidates, compare on identical eval slices, and validate on holdout cases. It includes supporting reference material on core prompt patterns, model-family adapters, and transformation examples.

Detected Capabilities

read reference filesanalyze prompt structure and patternscompare outputs across prompt variantsdocument external context dependenciesgenerate optimization logs and reflective memory

Trigger Keywords

Phrases that MCP clients use to match this skill to user intent.

optimize agent promptsystem prompt tuningport prompt across modelsprompt eval designimprove prompt reliabilityrewrite system instructions

Referenced Domains

External domains referenced in skill content, detected by static analysis.

agents.mdai.google.devarxiv.orgdevelopers.openai.comdspy.aiplatform.claude.complatform.openai.comwww.apache.org

Use Cases

  • Optimize underperforming agent or system prompts through eval-backed iteration
  • Port prompts across OpenAI, Claude, and Gemini while preserving behavioral contracts
  • Design prompt eval sets and establish success criteria before engineering
  • Refactor long or duplicated prompts by identifying causal layers and deduplicating rules
  • Build reusable prompt packages with external context inventories and adapter notes for different model families

Quality Notes

  • Exceptional structural clarity: six-step workflow is linear, preconditioned, and validates outputs. Each step names its input file and states its purpose.
  • Comprehensive reference architecture: core-patterns.md, meta-optimization-loop.md, and model-family-notes.md provide actionable depth without overwhelming the main workflow.
  • Strong sourcing discipline: SOURCES.md transparently documents all external references (OpenAI, Anthropic, Gemini official docs, research papers) with trust tier and contribution mapping. This is exemplary for a skill that synthesizes multi-source guidance.
  • Excellent anti-pattern documentation: transformed-examples.md shows before/after pairs with concrete rationales (e.g., replacing contradictory instructions with operational rules). This teaches by counterexample.
  • Precondition-aware: explicitly flags when prompt optimization is not the bottleneck (model choice, retrieval, tool schema, evals missing) and instructs to escalate rather than iterate.
  • Limitations honestly documented: SPEC.md and SOURCES.md acknowledge that prompt behavior drifts with model snapshots and that external file references depend on agent file access.
  • Model-family parity enforced: references separate OpenAI, Claude, and Gemini adapter strategies rather than assuming one-size-fits-all prompting. Compaction, XML tags, reasoning defaults, and tool disclosure all get family-specific notes.
  • High reuse value: output package structure (Target, Success Criteria, External Context, Optimized Prompt, Adapter Notes, Eval Set, Optimization Log, Residual Risks) is self-contained and portable across teams.
Model: claude-haiku-4-5-20251001Analyzed: Jul 11, 2026

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