Feedback on your automating-messages skill #6
Description
I took a look at your automating-messages skill and wanted to share some thoughts.
Links:
The TL;DR
You're at 96/100, solidly in A territory. This is based on Anthropic's best practices for skill design. Your strongest areas are Spec Compliance (14/15) and Progressive Disclosure Architecture (26/30) - the hub-and-spoke structure with separate reference files is really well done. The weakest area is Utility (17/20), mostly around feedback loops and degrees of freedom.
What's Working Well
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Spec Compliance is chef's kiss - Your YAML frontmatter is tight, name conventions are perfect (hyphen-case), and description triggers are well-chosen (iMessage, JXA, Messages automation).
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Reference architecture is smart - You've got 4 focused reference files (control-plane, database-forensics, monitoring-daemons, ui-scripting-attachments) that each stay under 60 lines. That's efficient token-wise and easy to navigate.
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Security awareness - You're not being alarmist, just factual about FDA requirements and the trade-offs of Messages automation. The validation checklist in SKILL.md gives developers a real run-check pattern.
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Working code matters - You've got SQL query templates, launchd plist guidance, and actual send/receive examples. People can copy-paste and adapt.
The Big One
Redundant safeSend implementations - You've got the safeSend function explained in both SKILL.md and control-plane.md with minor variations. This is eating into your token economy and creating maintenance burden.
Fix: Keep one canonical example in SKILL.md (the quick recipe version), then in control-plane.md just reference it and show the variations/debugging patterns. This cleans up ~10-15 lines and makes it clearer there's one way to do this safely. Impact: +2 points toward that 98.
Other Things Worth Fixing
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Security section is a bit verbose (lines 57-63) - It's repeating what your validation checklist already covers. Condense to a single bullet point: "FDA requires explicit user confirmation for read/send operations." That's it. +1 point
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Trigger phrases could be more discoverable - You've got good base triggers, but add phrases like "bulk iMessage sending", "read message history", "JXA automation gotchas". People search differently. +1 point
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Monitoring-daemons reference needs a TOC - It's not over 100 lines but it covers 3 different daemon approaches. A quick "Jump to: launchd / Continuous / Scheduled" bullet list at the top helps. +1 point
Quick Wins
- Consolidate safeSend → one canonical, link variations (+2)
- Trim security warning from 6 lines to 1 (+1)
- Add discoverable trigger phrases (+1)
- Add TOC to monitoring-daemons (+1)
That gets you to 99/100 territory - basically production-ready for any macOS automation toolkit.
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