This is likely due to the fact that you are encountering a prompt that iTest has not yet "learned". It is also possible that you are running your testcase on a different device that now has different prompts. For example, your prompt may have changed from "DUT-1>" to "DUT-3>".
The way to handle this is to update your session profile where you maintain your prompts. Make sure to use either a wildcard as shown in the screenshot below or regular expression. The regex for "DUT-1>" prompt would be
![alt text] : /storage/attachments/1872-prompts.jpg
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