Methods, systems, and apparatus, including computer programs encoded on a computer storage medium, relating to synthetic call initiations and bailouts. In some implementations, a method includes analyzing, by a call initiating system, a real-time conversation between a first human and the bot during a phone call between the first human on a first end of the phone call and the bot on a second end of the phone call. The call initiating system can determine, based on the analysis of the real-time conversation, whether the phone call should be transitioned from the bot to a second human on the second end of the phone call. In response to determining that the phone call should be transitioned to a second human on the second end of the phone call, the call initiating system transitions the phone call from the bot to the second human.