Let’s take a weather chat bot as an example to examine the capabilities of Scripted and Structured chatbots. The question “Will it rain on Sunday?” can be easily answered. However, if there is no programming for the question “Will I need an umbrella on Sunday?” then the query will not be understood by the chat bot. This is the common limitation with scripted and structured chatbots. However, in all cases, a conversational bot can only be as intelligent as the programming it has been given.
There is no one right answer to this question, as the best solution will depend upon the specifics of your scenario and how the user would reasonably expect the bot to respond. However, as your conversation complexity increases dialogs become harder to manage. For complex branchings situations, it may be easier to create your own flow of control logic to keep track of your user's conversation.
In 1950, Alan Turing's famous article "Computing Machinery and Intelligence" was published, which proposed what is now called the Turing test as a criterion of intelligence. This criterion depends on the ability of a computer program to impersonate a human in a real-time written conversation with a human judge, sufficiently well that the judge is unable to distinguish reliably—on the basis of the conversational content alone—between the program and a real human. The notoriety of Turing's proposed test stimulated great interest in Joseph Weizenbaum's program ELIZA, published in 1966, which seemed to be able to fool users into believing that they were conversing with a real human. However Weizenbaum himself did not claim that ELIZA was genuinely intelligent, and the introduction to his paper presented it more as a debunking exercise: