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Harden plan creation and execution reliability #988

@dcrjodle

Description

@dcrjodle

Summary

From Tendril Test Submission feedback: Some testers could not complete core workflows because onboarding, plan creation, or execution failed before reaching the product's main value. The plan creation and execution pipeline needs to be audited and hardened, particularly around missing assets, packaging assumptions, and startup timing issues.

Acceptance Criteria

  • Core flows succeed in clean test environments
  • Missing internal files are detected early
  • Known failures have regression coverage
  • Top reported blockers are reproducible and fixed

Additional Context

This issue addresses reliability concerns identified during Tendril testing that prevented users from reaching the product's core value proposition.


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Reported by Christopher Clemons

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