You can setup that relationship in your Discovery Connection for your Assets. In the Attribute Mapping tab look for Client User Names.
Ah, but the problem here is that it depends on how you are bringing in the Asset records.
If you are doing a WMI "Discovery Connection" task for the import of asset data, WHD can pull a decent amount of info from the boxes (CPU/RAM/OS version/MAC address/IP address/machine name/installed software/serial number/a few other things) but 'last logged on user' and/or 'client user name' are not options that can be associated in the Attribute Mapping tab for that kind of discovery.
So, although you can do a WMI discovery to find Windows assets, that info is not directly tied to AD info (which seems to be the request here).
If you are pulling assets in from another source (e.g. SCCM or Lansweeper for example) you would be able to map those fields in Attribute Mapping for that discovery task if the source has that data to match up.
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Yes, it does depend on the discovery method, you are correct on that
If you are not using a discovery connection that supports that option, then I would use a script to import the data.
First you would need a way to associate a user with a device dynamically. How you go about that would greatly depend on the size of your organization. You could use a GPO logon script that logs the user's logon to a file or DB. You could use a GPO startup script that reads the Win32_UserProfile WMI Class and dumps that data to a file or DB. You could parse event logs (on the PCs or on a DC). Etc etc etc
Second, once you have that data you can link the assets to the clients using the REST API ( Web Help Desk REST API Guide ).
Then it's just a matter of how often you need this to be updated and scheduling your script.