Assistant ignoring `.send`

I have an agent designed to conduct an interview. When the intended duration is nearing its end, I add a system message to tell the agent to summarize/conclude the call and say goodbye (kinda workaround solution to give the agent awareness of time in a way that hasn't been added natively)

Expected behavior:
The agent receives the message and concludes the call.

Actual behavior:
The agent receives the message (verified in call logs) and ignores it, continuing to ask questions.
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