One VM cannot get to intermedia hosted exchange servers - routing issues?

We have a terminal server that all of a sudden stopped being able to get to intermedia.net's proxy address for autodiscover. We cant ping it, the tracert fails with 50+ hops. Intermedia cannot ping the public address of the server in question, but we can from every other computer. We have other machines in the server farm without issues. 

 

Could google have a routing issue? Who / how do we contact someone, its our first actual issue with Google and first time needing support with them?

Thanks!

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So, we found that the test got out the gateway onto the internet but was dead after some Cloudflare ip. I emailed their noc and 10 minutes later the route changed. After 12 ours of it not, it must have just been a coincidence. I'm glad its fixed but what a nightmare!

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we ran a connectivity test from the nic which was successful. But not from the windows VM that uses that nic. Gotta love networking hell! 

So, we found that the test got out the gateway onto the internet but was dead after some Cloudflare ip. I emailed their noc and 10 minutes later the route changed. After 12 ours of it not, it must have just been a coincidence. I'm glad its fixed but what a nightmare!