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I have Debian Jessie 8 running on ESXi 6. The guest is configured with 3 virtual interfaces and each of the interfaces is assigned 1 static IP address but unfortunately, when I configured the IPs in /etc/network/interfaces the interfaces were misbehaving and I had commented them out to reconfigured them via GUI. Also, each of the interfaces has a static route to 3 different location and static routes are configured as persistent. However, each time the Guest OS is rebooted only the eth0 automatically come up for the rest I have to manually issue /etc/init.d/networking restart before they come up. I have another guest running CentOS with the same configuration inside the ESXi and is running without any issue. I have read many articles online no seems to work for me. Is there any other ways to configure persistent static routes on Debian Jessie. Below is my current configuration.