@Jason said:
Well proper routing might be needed and since he's this incompetent maybe routing isn't setup right. polish your resume and get another job.
While this is an isolated incident, @jason is right. You are dealing with someone who is missing very basic things. Things that a Windows entry level person would be expected to know. And while it is fine to miss things (maybe Windows isn't his background) he's missing "common use cases" on top of not knowing "standard entry level technology" and then "not understanding how to approach a problem" and using years out of date technology, too.
It's about four big red flags in a single incident. It's a situation where, for your own good, you want to question how good of a manager or mentor this person is for you. Are you likely to learn from them? Or find that they hold you back from learning and growing in your own career.