How do you update and migrate ISAPI applications to newer versions of IIS?

1 Assess your current ISAPI applications

The first step is to assess your current ISAPI applications and identify their dependencies, configurations, and compatibility issues. You can use tools such as the Web Deployment Tool, the IIS Migration Tool, or the Application Compatibility Toolkit to scan your applications and generate reports. These reports can help you determine if your applications are compatible with the target version of IIS, what changes are required, and what potential risks are involved.

2 Prepare your target IIS server

The second step is to prepare your target IIS server for hosting your ISAPI applications. You need to install the same or compatible versions of the ISAPI extensions and filters that your applications use on the source server. You also need to configure the IIS settings, such as the application pools, the security settings, the ISAPI and CGI restrictions, and the ISAPI cache settings, to match or optimize your applications' requirements. You can use the Web Deployment Tool or the IIS Migration Tool to export and import the IIS settings from the source server to the target server.

3 Test your ISAPI applications on the target IIS server

The third step is to test your ISAPI applications on the target IIS server before you migrate them. You can use a staging environment or a virtual machine to create a replica of the target IIS server and deploy your applications there. You can then use tools such as the Web Application Stress Tool, the Debug Diagnostics Tool, or the IIS Performance Monitor to test your applications' functionality, performance, and stability on the target IIS server. You can also use tools such as the Fiddler Web Debugger or the IIS Failed Request Tracing to troubleshoot any errors or issues that may arise.

4 Migrate your ISAPI applications to the target IIS server

The fourth step is to migrate your ISAPI applications to the target IIS server. You can use the Web Deployment Tool or the IIS Migration Tool to package and transfer your applications from the source server to the target server. You can also use the Web Deploy Command Line or the Web Deploy PowerShell Cmdlets to automate the migration process. You need to ensure that you migrate all the necessary files, folders, databases, and registry entries that your applications depend on.

5 Verify your ISAPI applications on the target IIS server

The fifth step is to verify your ISAPI applications on the target IIS server after you migrate them. You need to check if your applications are working as expected, if they are compatible with the target IIS server's features and security settings, and if they are performing optimally. You can use tools such as the Web Application Readiness Tool, the IIS Best Practices Analyzer, or the IIS Performance Tuning Tool to validate and optimize your applications on the target IIS server.

6 Update your ISAPI applications on the target IIS server

The sixth and final step is to update your ISAPI applications on the target IIS server as needed. You may want to update your applications to use newer or more efficient ISAPI extensions and filters, to leverage new or improved IIS features, or to fix any bugs or vulnerabilities. You can use tools such as the Visual Studio, the IIS Manager, or the IIS Administration API to update your applications' code, configuration, and deployment on the target IIS server.

7 Here’s what else to consider

This is a space to share examples, stories, or insights that don’t fit into any of the previous sections. What else would you like to add?