Yes @Mighty this behavior is expected and not a prompt issue. Advanced warm transfer is not supported for looping a call back to the same device or same call leg anymore. Recent Retell updates tightened human-answer detection and call-leg validation, so when the agent tries to hand off “you to you,” the second leg is treated as invalid and gets dropped. This is why it used to work for demos and now fails.
For reliable testing, you must use a separate phone number or device for the transfer target.