A network-based ambiguity resolving conversational understanding system, the system comprising: at least one processor; and memory, operatively connected to the at least one processor and storing instructions that, when executed by the at least one processor, cause the at least one processor to: receive, via a network, a speech input from a user computing device; identify an agent action based on the speech input; determine whether there is an ambiguity in the agent action; determine an ambiguity value associated with the ambiguity in the agent action; when it is determined that there is an ambiguity in the agent action, evaluate the ambiguity value against a criticality level associated with the agent action, the criticality level corresponding to a consequential severity of performing an incorrect agent action, wherein the criticality level decreases when the agent action is reversible; when it is determined that the ambiguity value meets the criticality level: select a prompting action based on the ambiguity in the agent action, wherein the prompting action comprises one or more of an audio feedback output by an audio component of the user computing device and a visual feedback provided on a display of the user computing device; initiate performance of the prompting action by the user computing device; receive additional input in response to the prompting action; and update the agent action to resolve the ambiguity based on the additional input; and initiate performance of the agent action. at least one processor; and memory, operatively connected to the at least one processor and storing instructions that, when executed by the at least one processor, cause the at least one processor to: receive, via a network, a speech input from a user computing device; identify an agent action based on the speech input; determine whether there is an ambiguity in the agent action; determine an ambiguity value associated with the ambiguity in the agent action; when it is determined that there is an ambiguity in the agent action, evaluate the ambiguity value against a criticality level associated with the agent action, the criticality level corresponding to a consequential severity of performing an incorrect agent action, wherein the criticality level decreases when the agent action is reversible; when it is determined that the ambiguity value meets the criticality level: select a prompting action based on the ambiguity in the agent action, wherein the prompting action comprises one or more of an audio feedback output by an audio component of the user computing device and a visual feedback provided on a display of the user computing device; initiate performance of the prompting action by the user computing device; receive additional input in response to the prompting action; and update the agent action to resolve the ambiguity based on the additional input; and receive, via a network, a speech input from a user computing device; identify an agent action based on the speech input; determine whether there is an ambiguity in the agent action; determine an ambiguity value associated with the ambiguity in the agent action; when it is determined that there is an ambiguity in the agent action, evaluate the ambiguity value against a criticality level associated with the agent action, the criticality level corresponding to a consequential severity of performing an incorrect agent action, wherein the criticality level decreases when the agent action is reversible; when it is determined that the ambiguity value meets the criticality level: select a prompting action based on the ambiguity in the agent action, wherein the prompting action comprises one or more of an audio feedback output by an audio component of the user computing device and a visual feedback provided on a display of the user computing device; initiate performance of the prompting action by the user computing device; receive additional input in response to the prompting action; and update the agent action to resolve the ambiguity based on the additional input; and select a prompting action based on the ambiguity in the agent action, wherein the prompting action comprises one or more of an audio feedback output by an audio component of the user computing device and a visual feedback provided on a display of the user computing device; initiate performance of the prompting action by the user computing device; receive additional input in response to the prompting action; and update the agent action to resolve the ambiguity based on the additional input; and initiate performance of the agent action.