Here you need two adapters as clicking on website should be handled by web adapter and clicking on Open window should be handled by windows adapter. Always start Web adapter and then start windows adapter, then only Window screen controls can be interrogated.

Steps to Configure both Adapters:

1. Create a web adapter. In web adapter properties perform below changes.

• StartMethod = MonitorAll
• StartPage= https://test.com/test.html
• HookChildProcesses= True

2. Create a windows adapter. In windows adapter properties perform below changes.(in "Arguments" property specify "StartPage" property that you have specified in web adapter)

• Arguments=https://test.com/test.html
• Path=C:\Program Files\internet explorer\iexplore.exe
• HookChildProcesses= True

Steps to Start Interrogation:

1. Click on Start Interrogation button on Web Adapter. wait till bulls eye pops out.

2. Click on Start Interrogation button on Windows Adapter.

Note: Follow above steps in specified order.

You will be having two bulls eye windows for two adapters. You should be able to interrogate using windows adapter bulls eye window. 

I see you have attached Chrome screenshot, of the windows control. But I hope you were requesting steps to interrogate. Hence try to interrogate with either of the adapters.