Developer hits four dead ends trying to build Apple Shortcuts programmatically

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A developer attempted to automate publishing to a REST API using Apple Shortcuts, building a three-step shortcut that lets Siri dictate and POST content directly to an endpoint. While the shortcut worked fine when built manually on-device, every attempt to create, sign, or deploy it through code failed. The macOS 'shortcuts sign' CLI rejected hand-written property lists and, on macOS 14.6, returned an iCloud authentication error even on valid files with iCloud fully enabled. The URL import scheme only accepted links hosted on Apple's own icloud.com domain, blocking any self-hosted or third-party file imports. The only partial workaround discovered was reverse-engineering an undocumented iCloud API endpoint that returns unsigned, readable shortcut plists from shared links.

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