Iis – HTTP Error 500.19 – Internal Server Error

The problem your seeing is addressed on the NAS' FAQ page under "How to solve security problems with drive mappings, under Windows Vista?"

First, follow the instructions on the FAQ page, they should also apply to Win2k8:

The security policies which are being used by Windows Vista are not supported by the Samba software in the 'network storage device'. Therefore, to use file shares/folders of your 'network storage device', you need to change this the security policies of Windows Vista.

2. Map a network drive to the NAS on your IIS server and connect as "Guest".
3. Point your website's Local Path to that network drive.
4. You'll have to grant the IUSR_ account access to the share on the Win2k8 box, but it won't matter that IUSR_ doesn't exist on the NAS, since the drive was mapped with "Guest".

You might have to change the security of "Guest" on the NAS.

That errors means that you have a duplicate setting for UrlRoutingHandler. It's probably set in C:\sites\website1\ or applicationHost.config. You should be able to delete that line from the web.config file for \dd\web.config and you'll be set. To find the root cause, check the other config files in the tree (site level, applicationHost.config in this case) for UrlRoutingHandler.