App Insights: Telemetry not showing User data

Hello,

I have my .Net Core app and I've added ITelemetryInitializer and got that all set up. In Application Insights for that app, under Performance => Operation Name => Samples => Suggested => Request Properties -> Show All => "Auth Id" and "Account Id" have values now, great.

Now, in Application Insights => Users, I still only have 1 User. How do I get the Usage/Users functionality to read the User information that the requests under performance are collecting?

I've read lots of MSFT documentation on https://docs.microsoft.com/en-us/azure/azure-monitor/app/usage-send-user-context and https://docs.microsoft.com/en-us/azure/azure-monitor/app/usage-troubleshoot#counting-users, but no luck. It seems like if I have "anonymous user ID, authenticated user ID, or session ID" in the Request Properties, the Usage telemetry should be picking it up. 

Any suggestions?