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I'd really like to understand how to debug my network connectivity issues, but everything I find on the internet is either for basic users on "How to add a wireless network" or it's people talking about enterprise-grade networking problems with Cisco routers.

For example, I have a Win2k8 R2 Box running with Hyper-V, and I tried to share my wireless connection in two ways: bridging the wireless connection and the virtual connection or turning my Windows 2k8 box as a router and making the NAT feature translate requests from the virtual machine to the outside world.

Now both of them work...sometimes. And then sometimes they just stop working. Sometimes if the host wireless is connecting to a proxied internet connection, it fails.

And this is where I'm generally stuck because I have no idea what to do to debug? How can I troubleshoot the problem beyond a. disconnecting and reconnecting and hoping everything magically works (rarely does) b. cursing at my computer (never) c. deleting the connection and recreating it all over again (sometimes works).

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I would start by doing a traceroute to google.com and to 8.8.8.8. If google.com fails and 8.8.8.8 succeeds, it's bound to be a DNS issue. If both fail, you can see where they hang. That should be a good first hint.

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both tracert & ping to google.com & 8.8.8.8 work. But if i try to browse to google.com, I get a connection problem –  Ikrima Elhassan Mar 9 '11 at 13:32
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