Conversation failures are hard to test because they depend on everything said before. The trick is the same as in lesson 19: find the first turn that went wrong. Everything after it may only be fallout.
Then reproduce it in its smallest form: replay the turns before the failure (N−1 turns) in one conversation, send the failing turn, and assert what should have happened. That gives a short, fast regression test instead of a long scripted chat.
Your task
- Read the customer's conversation and name the first turn where OrderDesk failed.
- Write a test that replays only the turns before it, sends the failing turn, and checks the outcome. On submit it runs on a working agent and on the build that loses context.