Getting HTTP Error 500.19 - Internal Server Error when trying to access old ASP classic web site on Windows 2016 Server

Question

I've had to port an old ASP Classic application to Windows 2016 Server. It is configured as a virtual directory in IIS Manager (not IIS 6.0 Manager) and I made sure to install IIS 6.0 Compatibility beforehand. The site is set up for anonymous authentication and a simple default document of index.asp. When I try to browse the virtual directory right in IIS (by right-click on the virtual directory name in the left-hand pane in IIS --> Manage Application --> Browse) I get a HTTP Error 500.19 - Internal Server Error when trying to access old ASP classic web site on Windows 2016 Server error. Please see the attached screen shot jpg file that I've attached. The error tells me that the anonymous authentication specification in the virtual directory's Web.config file is invalid because it cannot be placed where it is in the Web.config file. More specifically, the verbose config error details (see screen shot) refer to overridemodeDefault settings that I would need to change from "Deny" to "Allow" in the applicationHost.config file under "C:\Windows\System32\inetsrv\config" to get around this problem. I have gone in that file under <sectionGroup name="system.webServer"> and under <sectionGroup name="authentication"> I modified <section name="anonymousAuthentication" overrideModeDefault="Deny" /> to "Allow". After doing so I restarted IIS and tried browsing again, getting same result. I then rebooted the server on the possibility that this takes a reboot, but still same results. The last piece of information I would like to add is that originally I linked the virtual directory to the DefaultAppPool application pool per what I had seen on a comparable successful setup, though I noted that that this application pool is associated with .NET v4.0 (also Integrated for Managed Pipeline Mode and ApplicationPoolIdentity for Identity). I tried switching to the .NET v2.0 Classic application pool which is associated with .NET v2.0 CLR and Classic for Managed Pipeline Mode.

Thank you for any help you can offer.

99188-web.txt

Answer 1

Hi @aramb1958

You can try the following methods to solve the problem.

1. Go to server manager, click add roles and features
2. In the roles section choose: Web Server
3. Under Security sub-section choose everything
4. Under Application Development choose .NET Extensibility 4.5, ASP.NET 4.5 and both ISAPI entries
5. In the features section choose: ASP, .NET 3.5, .NET 4.5, ASP.NET 4.5
6. In the web server section choose: Web Server (all), Management Tools (IIS Management Console and Management Service), Windows Authentication - if you are using any of it.

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Answer 2

@Sam Wu-MSFT - sorry, this should be posted as "Reply" but I found I could not submit Replay (???)

No luck yet. I found some differences between your instructions and the site server.

In Web Server...

1. Security: Chose everything per instructions.
2. Application Development:
   a. Found .NET Extensibility 4.6 & ASP.NET 4.6 rather than 4.5 versions. So I chose these instead.
   b. Found .NET Extensibility 3.5 & ASP.NET 3.5 already chosen so I left them that way.
   c. Also found ASP already chosen so I left it that way.
   d. Chose both ISAPI entries.
   e. Also found Server Side Includes & Application Initialization chosen & left them that way.

Found Features separate from Server Roles. Related things here were:

1. .NET Framework 3.5 Features under which .NET Framework 3.5 (includes 2.0 & 3.0) was already chosen
2. .NET Framework 4.6 Features under which .NET Framework 4.6 & ASP.NET 4.6 were chosen.
   a. Also WCF Services -> TCP Port Sharing was chosen as well.

I installed, restarted IIS & browsed web site with same results. Thanks in advance for help.