The whole point of this post was to get advice, not to be insulted. I'm new to the field, and documenting everything is a valuable lesson I've learned. My boss can be unpredictable, and there's no good reason for not upgrading a system that only runs a single program and has significant security risks. I already plan to send the CYA email tomorrow and then drop it.

I'm not going over anyone's head. The employee who needs the machine is the one asking for the upgrade because it's impacting his work. He's been requesting it for 8 months. Your attitude is unhelpful, and you're making faulty conclusions. Just because I'm new doesn't mean I don't have valid concerns.

I'm looking for advice to handle this professionally, not to be made to feel bad for asking for help. Maybe next time, try offering constructive advice instead of acting superior.