Hello @Rich Hamack
I'm glad your issue was resolve and thanks for posting the solution so that others experiencing the same thing can easily reference this!
Since the Microsoft Q&A community has a policy that "The question author cannot accept their own answer. They can only accept answers by others", I'll repost your solution in case you'd like to "Accept " the answer.
Issue:
-Application insights failing to load telemetry - Azure App service, .net 4.8
-The application was initially configured manually in Visual Studio, but then all application insights NuGet packages were removed in favor of using the built-in agent in Azure App Service.
-At first everything worked fine, but then the telemetry disappeared.
Solution:
"I found the actual problem. After I cleared out the set of DLL's from the project, I was deploying via Azure DevOps to the application service. I had not checked the box to clear out all existing files in the service which were not included in the deployment (to see this checkbox, we now need to manually select a deployment method). After selecting this option in the release, the old assemblies were cleared out of the app service bin folder, which removed the conflict. Application Insights began collecting and correlating telemetry from that point on."
Thanks again for sharing your solution.
Best,
Grace