In a system for managing chat automation, the system includes: a processor; and a memory coupled to the processor, wherein the memory stores instructions that, when executed by the processor, cause the processor to: receive a signal indicating a communication is being initiated by an end user operating an end user device; receive information from the end user device regarding the communication; select a conversation path based on the information regarding the communication; invoke an automated chat resource for engaging in a chat communication session with the end user device, wherein the automated chat resource is configured to follow the conversation path during the chat communication session; monitor confidence levels of automated chat responses during the chat communication session; and redirect the chat communication session to a second conversation path in response to at least one of the confidence levels falling below a threshold level.