How to find the host / IP address an application is trying to reach and fails?

Question

I am trying to enroll a Windows 11 system in a Workspace One environment by using some Powershell script.
Everything is successful, the system gets enrolled fine.
However when I open the Intelligent Hub Application it shows that is not enrolled, that's because it's trying to reach some server - it says "not connected"
How can I find out which host / IP is some Windows application/process trying to reach without success ?
I have tried Wireshark, but I am lost in that tool also.

Answer 1

I would like to ask more questions about your case but I don't have the reputation to comment so I'll answer your question with my impressions directly.

When you say "Everything is successful, the system gets enrolled fine." I'm guessing you are referring to the Workspace One UEM console, meaning that you can see the device enrolled, is there any prompt or warning? Is it truly connected + WNS shows connected on the console? Does it have a last seen according to the device connection?

You can try extracting some logs from the computer using the event viewer, you may find which host the device is trying to access once you send the command line to enroll it and check the events, though my guess is that it is not reaching properly your console host. I never enroll Windows devices via powershell (I enroll them installing the Intelligent Hub app and entering the server host and group ID) so I'm not sure how it would be, but you can check just in case if the server host name (which you can check in Group & Settings > System > Advanced > Site URLs) is spelled properly or if it is missing some parameter.