I was pinging from Windows 2012 R2 machine to a Windows 2016. Both are multi-homed boxes, Windows 2012 R2 have 3 NIC cards, Windows 2016 got 4. Windows will try to figure out the best interface to use by determining the quality of network connection - which eventually shows up as the metrics of the interface. The lower the metric number the higher the order of preference. In one case, I had 2 network interfaces on flat network (no routing) and one interface that is routed but has the lowest metric. The issue was that that one network thinks it has the IP of the given NetBIOS name but was actually pointing to wrong IP, it seems like one of the routers have cached the IP incorrectly. Tracing where it was cached is not easy specially so if you don't have control of the network. Anyway, since the box actually have 3 direct connections to the other unit and it refuses to use the other network interfaces, the best option was to modify hosts file (C:\Windows\System32\drivers\...
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