Switching SharePoint from Secured to Anonymous Access - Problems have Arisen

Question

Background:
We had SharePoint setup by a professional SharePointer several years ago to be secured from anonymous Access.  Documentation was non-existant except showing us how to setup new sites and a few other things.
Goal:
We are trying to remove the login only access and switch it so that people can see the front page and a few select subpages anonymously.  We are in the midst of a repurposing.
Problem:
I have followed the instructions at this
site and the first thing that happens when we go to the site is that we are prompted to login.  We are thinking that the professional set something else somewhere to force it to prompt.  Any help with this would be appreciated.
Troubleshooting:  On top of the basic setup I have double checked permissions on all Sites and folders making sure that there is nothing on the main page that isn't allowed Anonymous Access. Have also fiddled with IIS settings, but to no avail (the
settings have been returned to normal).
Also, please note that my AnonymousPermMask64 is set to:
ViewListItems, ViewVersions, ViewFormPages, Open, ViewPages, UseClientIntegration

Answer 1

Hi,
According to your post, my understanding is that you wanted to enable the anonymous access for the site.
As you had enable the anonymous access in web application and site level following the instructions, and still could not enable the anonymous access.
To narrow down the issue, we can do some steps as below.
First, we can create a new site in the web application, then enable the anonymous access for the site.
If the site could anonymous access, the issue would occur in your old site.
Then we can check the steps for anonymous access in the old site, or we can also check ULS log to see if anything unexpected occurred.
For SharePoint 2010, by default, ULS log is at
C:\Program Files\Common Files\Microsoft Shared\Web Server Extensions\14\LOGS
What’s more, we can also back up the site collection, then restore the site collection to check whether it works.
http://technet.microsoft.com/en-us/library/ee748617(v=office.14).aspx
http://technet.microsoft.com/en-us/library/ee748655(v=office.14).aspx
Second, if the new site still could enable the anonymous access, the issue would occur in the web application level.
You should check the issue with the web application as above.
You can also backup the web application restore to a new web application to check whether it works.
http://technet.microsoft.com/en-us/library/ee748623(v=office.14).aspx
Thanks & Regards,
Jason
Jason Guo
TechNet Community Support