Usually when you start a conversartion with Umboto, it will try to offer you all the knowledge it has be trained on. But there are somethings that only humans can do ;)
The best way to request a downtime investigation would be to choose "Site Down" and then "Downtime Investigation."
In case you don't have access to this workflow, just type "talk to a human", and Umboto will connect you with one of our teammates.