Browsing to any package via HTTP or HTTPS in IIS results in HTTP Error 500.21 - Internal Server Error. The detailed error indicates: Handler "StaticFile" has a bad module "DirectoryListingModule" in its module list.
ITMS 8.x
The Directory Browsing module/role service is missing from the Web Server (IIS) role.
Although missing this module does not prevent endpoints from downloading packages, installing it is recommended for troubleshooting virtual directory access over HTTP or HTTPS.
Steps to resolve:
Open Server Manager on the Notification Server / IIS host.
Click Manage > Add Roles and Features.
Navigate through the wizard to Server Roles.
Expand Web Server (IIS) > Web Server > Common HTTP Features.
Check the box for Directory Browsing.
Complete the wizard to finish installing the feature.