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Below is what gets returned when running the file from the terminal:

"Retrying due to transient client side error HTTPSConnectionPool(host='westus-0.in.applicationinsights.azure.com', port=443): Max retries exceeded with url: //v2.1/tr ack (Caused by ProxyError('Cannot connect to proxy.', OSError('Tunnel connection failed: 403 Forbidden')))."

My Azure resource is up and running and my desktop app is able to successfully send telemetry. In the past I have had DNS (Adguard specifically) cause connections to fail to Azure. Since this web app is all hosted, and my desktop app is currently sending telemetry I am inclined to believe its an issue on PythonAnywhere systems. Any help or guidance is appreciated.

The proxy error suggests that you're trying to connect through the proxy, which is not necessary since you have a paid account.