The Session

Started with “can I build an iOS Shortcut from a text file?” and ended with 8 working shortcuts, a documented Apple bug, and a comprehensive Cherri guide.

Hello World to Crash Loop

The first shortcut was a notification. Compiled, signed, imported — smooth. Then we tried building shortcuts that hit web APIs with dynamic URLs, and the Shortcuts app started crashing on import. Not just failing — crash-looping. The app wouldn’t open at all.

The culprit: variable interpolation inside URL and header strings across multiple web request actions. Apple’s WFAppKitAutocompleteTextView throws a layout exception during the import parsing phase. This is an Apple bug in the Shortcuts import UI itself.

We found it through binary search: strip half the actions, test import, narrow down. The fix was to hardcode all URL strings. The crash-loop fix was deleting ~/Library/Saved Application State/com.apple.shortcuts.savedState.

Reverse Engineering

Used cherri --import=<icloud-url> to decompile existing shortcuts from iCloud links. Pulled apart “How’s My Cinder” and “Magic Market Analysis” to learn the action vocabulary. This is the fastest way to learn Cherri — find a shortcut that does what you want and read the decompiled source.

The Synology-Garden Audiobook Shortcuts

Built three shortcuts that talk to the shortcut-bridge API running on the NAS:

Surprise Me — picks a random audiobook and asks ChatGPT for a pitch
What’s Next Book — recommends the next book based on listening history
Library Digest — full library stats with AI-generated insights

All three had to use hardcoded URLs to avoid the interpolation crash. The pattern: compute any dynamic values first, then pass them as body parameters to a web request with a static URL.

Five Parallel Agents, Five Complex Shortcuts

The final push was five shortcuts built simultaneously by separate agents:

Weather Commander — 17 actions, queries 5 weather categories, formats a comprehensive briefing
AI Debate Club — runs a 3-round debate between ChatGPT, the device LLM, and Apple’s cloud LLM on any topic
Shazam DJ — identifies a song, analyzes it, generates anime-style album art
Digital Wellness — pulls screen time data and runs it through AI behavioral analysis
Voice Researcher — dictation to web research to flash card generation pipeline

All five compiled clean and imported without crashes. The hardcoded-URL pattern held. No merge conflicts because each shortcut is a standalone .cherri file.

What Shipped

8 working iOS Shortcuts (3 simple, 5 complex)
Comprehensive Cherri compiler guide
Claude Code skills for shortcut building
Project CLAUDE.md for the shortcuts-agentic repo
Documented crash bug with workaround

Pattern Notes

The Cherri compiler turns shortcuts into versionable text files. That alone is valuable — Apple’s visual editor has no diff, no review, no automation story.

The parallel agent pattern continues to compress time. Five independent shortcuts is a clean decomposition: no shared state, no coordination needed beyond “use hardcoded URLs.” Two hours of wall-clock, five complex shortcuts.

The crash bug discovery was the session’s real value. Without the binary search testing approach, we’d still be guessing why imports fail. Now there’s a documented workaround and a clear rule: never interpolate in web action URLs.