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I have a new windows 2008 web edition x64 server that I am running several ASP based web sites on, each on it own port. I have imported a wildcard pfx certificate and bound it to the web site and https works fine. The problem I have is that whenever I reboot the system IIS, Remote desktop and several other services hang. Also the initial configuration tasks app that normally displays information about the system name, time zone, roles, etc displays "loading" for all these items.

Booting into safe mode, removing the cert and rebooting returns the system to normal. I can then re-import the certificate and everything works fine until the next reboot. I have another system with the same config that is working fine.

I have had similar issues with windows 2008 systems when they have had bad entries in the machine.config under .net, but that does not seem to be the case this time.

No errors appear in the event log when the server boots in this state.

Any Ideas as to what is going on?

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2 Answers

Does the SSL certificate have a password/passphrase that is required? Could it be this that is causing IIS to hang?

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Yes but it installs fine using the passphrase. it is also the same one I have used to install on other systems. Also verified systems files. –  Anonymous Aug 14 '09 at 17:59
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I have been going through this off and on for a while and thought it was a VMWARE Problem. But its a certificate issue that I can reproduce 100% of the time. First you may notice that if you delete the cert or remove the binding, reboot, and the services start fine. Import it again, reboot, and they will hang. It had to do with the missing Intermediate Certificates from GoDaddy. Here is the fix for me. Remove the imported certificate. Follow the instructions to install the Intermediate Certificate Bundle on the Server from GoDaddy.

http://help.godaddy.com/article/4801

Then import your wildcard certificate and apply the bindings to the website.Reboot and all is good...

This was happening to me with an Exchange Client Access (OWA) server... Very frustrating, but this post got me started exploring the certificates, since this was the last thing I applied before the server flipped out. Apparently, the export does not include the whole certificate chain, so you have to apply the intermediates before the import of the wildcard. I hope this helps...

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Thanks AnExchangeUser! You pulled our frawns from the fire with your solution. Our Win2008EESP2 virtual machines running web services that had been running for months were completely hosed after applying Windows updates to the Win2008EESP2 host. No network connectivity, most automatic services would not start, just totally hosed. We were on the phone with MS support for hours with no resolution. Started rebuilding the virtual machines from scratch and noticed the problems occurred after binding a godaddy wildcard cert to the web service and rebooting. Googled the symptom and your solution popp –  user56475 Oct 7 '10 at 21:30
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