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Our corporate network has some web applications hosted in a nested subdomain hierarchy. A "subdomain's subdomain", as you will. For example:

  1. Root-> http://*.mydomain.com (resolves to: 192.2.2.200)
  2. App1-> http://application1.server1.mydomain.com (resolves to: 192.1.1.101)
  3. App2-> http://application2.server1.mydomain.com (resolves to: 192.1.1.102)

The problem is that when browsing to one specific app, let's say App1, the generic wildcard is returned. This is a simple landing page on Root. It works perfectly on any given Windows machine, and even some other Macs, but I can't seem to connect using a specific Mac OSX machine (OSX 10.7.3).

App2 works just perfectly in the browser.

Some performed checks:

  • The DNS has been setup correctly.
  • Pinging the address works - and resolves the correct DNS
  • Browsing to it using Safari, Chrome, Firefox etc. doesn't and seems to resolve to the main domain (1.)
  • Windows 7 on the same Mac (using Parallels) does work and resolves the correct webpage
  • The /hosts file is clean and has no relevant entries
  • There is no proxy, firewall or other app that I'm aware of that could interfere
  • I have used dscacheutil -flushdns without effect
  • Cleared browser cache, rebooted system etc.

It's almost as if the DNS locally on this machine isn't updated correctly - and still has a version of a month ago in it's cache. Or that someone goated the hosts file (verified, not the case).

Any ideas?

UPDATE: If I manually add an explicit entry to the /etc/hosts file, like 192.1.1.101 application1.server1.mydomain.com, everything works perfectly. However, if I remove the line again - the problem re-appears.

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Very curious. Do other websites' nested subdomains function properly? –  timothymh Mar 9 '12 at 11:33
    
What is the web server? IIS? Apache? Other? –  Stu Wilson Mar 9 '12 at 12:29
    
@TimothyMueller-Harder: yes they do. As stated, App2 works perfectly. –  Moriarty Mar 9 '12 at 12:57
    
@StuWilson: App1+App2 are Apache servers. Root is an IIS server. –  Moriarty Mar 9 '12 at 12:57
    
I know you said the DNS is set up correctly, but have you got specific entries in the Windows DNS for the apache servers themselves as well as aliases for the subdomain sites? I'm think Reverse DNS Lookup failure is a possible culprit. –  Stu Wilson Mar 21 '12 at 13:21

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