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Thanks for the precise report — the flag-symbol observation and "a 2-character new message fails identically" are the two facts that pin this down. Here is the mechanism, and a plugin-shaped answer to both halves of your question (localization + a session-level bypass).

Why the session, not the turn, is broken

Nothing about your new message is being rejected. The request that fails contains the whole conversation: the loop re-derives it from the session log on every call, and GenerateOptions.messages is documented as "ordered conversation messages, exactly as the provider sees them" (packages/llm/llm/src/types.ts:455-467). The rejection is a property of content, not of a turn — so once on…

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