Define the failed path
Write down source, destination, protocol and port. A failed ping and a failed TCP connection are different symptoms.
Check DNS
Confirm that the source resolves the destination name to the expected private or public address. Test the resolved address directly when possible.
Check NSGs on the network interfaces
Review inbound and outbound NSG rules attached to the relevant network interface and subnet. Look for a lower-priority deny that blocks the intended flow.
Check routes
Use Network Watcher connectivity checks and review user-defined routes when traffic is sent through a network virtual appliance or another next hop.
Test the actual port
From Windows, use Test-NetConnection destination -Port 443 or the application port. This gives a more useful signal than ICMP alone.
Validate the application
If TCP connectivity succeeds but the application still fails, inspect the listener, certificate, application configuration and backend dependencies.
Useful commands
Test-NetConnection <destination> -Port 443
Resolve-DnsName <destination>
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