This is similar to the issue asked here in SE before Why are user permissions set in AD not updated immediately to SharePoint? but in my case it doesn't work.
I have a SharePoint 2010 Enterprise Portal. Authentication mode is Claims based with NTLM. We have also published the portal via TMG.
I noticed something weird with Active Directory Group membership that doesn't update immediately in SharePoint when a user is removed or added to AD Group.
I have setup a SharePoint Group and added the AD Security group inside this SP Group. Users are added and removed via AD Security Group. I have setup publishing page with unique permission with members in SP group can only access. When I add a user in AD it doesn't get immediately reflected in SharePoint. As mentioned in SE article above it take 24 hours to update.
I ran this command to set the value to 1 minute(as mentioned in the post above) but no luck. But if I add the users directly to SharePoint Group it works immediately. There is something strange with Active Directory and SharePoint Synchronisation.
stsadm -o setproperty -propertyname token-timeout -propertyvalue 1
IISRESET
If I do a IIS Reset then the user permissions are properly updated. I have also set the User Profile service to run every 30 minutes(Incremental update).
Additional Info: The AD group scope is "Global" and group type is "Security".
Does anyone come across similar issue and fixed it?
Additional references
http://technet.microsoft.com/en-us/library/cc287917(office.14).aspx