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We are planning to perform an Rolling Pool Upgrade using the "automatic method" described in the Citrix XenServer ® 6.1.0 Installation Guide (at http://support.citrix.com/servlet/KbServlet/download/32308-102-691301/installation.pdf)

In order to use the "Automatic Mode" (to avoid installing with media at each host), we attempted to set up a local HTTP repository (or mirror) with the contents of the ISO. We chose this method because we have no NFS or FTP services in place, currently.

Because it was handy, I added a virtual directory (named "media") to an existing IIS web instance and enabled Directory Browsing (mostly for troubleshooting). Then I extracted the ISO into a sub-directory (named "xenserver-6.1") and verified the directory listing matched the contents of the ISO.

At this point I thought I was ready and I performed a test install using HTTP as the method and the address ("http://servername/media/xenserver-6/1"). When this test failed, I began researching the required contents of the directory and several other theories.

Jim Herrick
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The root problem ended up being unspecified MIME Type entries required for IIS to serve the contents of this directory. You can read more about this problem here: http://support.microsoft.com/kb/326965

To solve the problem, I added a "*" entry using the "application/octet-stream" MIME Type in the configuration of the virtual directory.

Credit to "Don Nelson" in this thread for pointing out the solution: https://forums.citrix.com/message.jspa?messageID=1604878

Note: Several hours were spent on this solution, mostly with research and troubleshooting. I have added this question (with an answer) to hopefully make this easier on the next person.

Note: Based on the nature of XenServer, I assume this "fix" may apply to other Linux-based installs.

Jim Herrick
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Realise this is answered and it helped me a lot in getting my servers configured. However I want to raise an issue that people may encounter (and that I did) if you are intending to use IIS7/7.5. What happened to me was that I entered the wilcard mime type, and it would serve any file that had an extension it didnot have explicitly defined, however it would not server extensionless files (and this is needed for the xenserver install).

In the end I discovered its a bug in a certain config of IIS7/7.5 on Windows 2008

https://support.microsoft.com/en-us/kb/2646735

Now I have to say I did not apply the hotfix, I moved to a windows 2012 R2 server running IIS8.5 and entering the wildcard mime type here allowed me to get this working...

I have put together a rushed blog entry here

http://mumblestiltskin.blogspot.com.au/2016/01/xenserver-installation-over-idrac.html

Mumblestiltskin
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    It would be much better to make this an actual question and answer. e.g. "Why does IIS7/7.5 not serve extensionless files needed for Xenserver Install?" then you can come back and answer the question a day later and score more points. :-D – tudor -Reinstate Monica- Jan 08 '16 at 04:25