Can't connect to SOME subnet addresses

My company uses OpenVPN to connect to some CenturyLink VMs. We have 4 VMs in total:

• 10.120.95.12
• 10.120.95.15
• 10.120.220.36
• 10.120.230.37

The two X.X.95.X addresses seem to connect just fine. I can PuTTY in like nothing's wrong!

The two X.X.220.X addresses have been giving us a whole hell of a lot of issues the last two mornings. Both days we've rolled into the office (or WFH like in my case) to find that we just can't get any connectivity at all!!

I'm not the network admin. Honestly you'll all probably hate me, given how little I understand, but I'm the only resource I've got at the moment with my boss (the network admin) on vacay this week.

Anyway, my gut said to run a tracert and see what comes up. Here are the results:

Traceroute to 10.120.95.12 (Working as far as we can determine)...

Tracing route to 10.120.95.12 over a maximum of 30 hops: 1 29 ms 29 ms 29 ms 10.255.220.1 2 30 ms 30 ms 30 ms 10.120.220.1 3 30 ms 29 ms 30 ms 10.120.95.12 Trace complete. 

Traceroute to 10.120.220.37

Tracing route to 10.120.220.37 over a maximum of 30 hops: 1 29 ms 30 ms 30 ms 10.255.220.1 2 10.120.220.230 reports: Destination host unreachable. Trace complete. 

So outside of speaking to a CenturyLink rep (they'll be calling back in a few hours), what can I do with this information? Does anyone have any crackpot theories? Am I unaware of a very useful troubleshooting step?

Seriously—any help would be super appreciated!