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I have a server named BlackBerry. I've assigned it the IP address of 192.168.1.211 from the DHCP on our router. On BlackBerry I have installed a virtual machine, Dev1, that uses a bridged network adaptor and gets the IP of 192.168.1.206. Both run Windows Server 2008 R2. I also have a Mac, running OS X Lion with a dynamic IP address.

I'd like to be able to access the different computers by their names or custom URL's instead of IP addresses. I've set up DNS on BlackBerry (192.168.1.211). I put the records in a dev domain (e.g. BlackBerry.dev). I have an A record for BlackBerry and Dev1 with their appropriate IP's. Running nslookup BlackBerry.dev returns 192.168.1.211. I can run nslookup from the mac or either of the Windows machines.

Both Windows machines run IIS and can be accessed via their IP addresses. Type in http://192.168.1.211 in any browser and I get the right webpage. But if I type Dev1.devin the address bar, it can't find the page. Same thing for RDP. But using the IP addresses works.

What am I doing wrong? Why can't I type BlackBerry.dev into an address bar and get the webpage hosted by that IIS?

Edit I have configured the DNS in the router to resolve to 192.168.1.211 (BlackBerry). That is why nslookup works, I think.

Edit 2 Sporadically works. Sometimes I can ping blackberry.dev and sometimes I can't. For instance, I just successfully pinged the server, ctrl-c to stop, then pressed the up arrow (to repeat the command) and all of a sudden it can't be pinged.

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It sounds like your Mac isn't configured to use Blackberry as its primary DNS server. More likely, it's using the default DNS server assigned by DHCP which forwards DNS requests up to the internet. Blackberry.dev isn't valid on the internet, so your Mac doesn't know how to resolve it.

To solve this, you either need to manually set the DNS server on your clients (Mac) to be 192.168.1.211, or configure your router to give out the DNS address on DHCP leases as 192.168.1.211. All clients should then resolve their DNS via Blackberry, and anything that's regular internet DNS resolution should be forwarded by Blackberry to your actual ISP nameservers.

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  • Sorry, forgot to mention that. I have the DNS of the router set to 192.168.1.211 (BlackBerry). Running nslookup BlackBerry.dev from the Mac correctly returns 192.168.1.211. I thought that if nslookup returned the IP address, I had everything set up correctly. Is that not right? – Tyler DeWitt Oct 29 '11 at 20:59
  • Two things: 1) Can you ping BlackBerry.dev from your Mac, and 2) Can you check that 192.168.1.211 is the only nameserver your Mac has configured? I'm not a Mac user, but ifconfig -a on Linux or ipconfig /all on Windows would be able to tell you this. – growse Oct 29 '11 at 21:28
  • Good call. I can't ping blackberry.dev. What am I looking for in the ifconfig -a? – Tyler DeWitt Oct 29 '11 at 21:34
  • I'm sorry, had a dim moment - ifconfig -a won't tell you about DNS, you'll want to do something like cat /etc/resolv.conf. Don't know if resolv.conf is the authoritative place for DNS servers on a Mac, but it usually is on many *nix systems. – growse Oct 29 '11 at 21:38
  • There are 3 nameservers: 192.168.1.211, the router its plugged into, and the router that that router is plugged into – Tyler DeWitt Oct 29 '11 at 21:47

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