This one caused a friend some headache when setting up a switched internet connection which had zero padded IP addresses in the configuration paper like so:
192.168.019.254
No matter how he tried to configure the Mac network stack, it just didn't work. But the GUI also didn't complain about errors.
I later found out that pinging these zero padded addresses in a terminal showed "unable to resolve" while pinging the same address without padded zeros (192.168.19.254 vs. 192.168.019.254) showed "unable to reach" which brought much light into this mysterium. Removing the useless zeros made everything work.
Is this a bug or a feature? I never experienced such strange behaviour before - no matter if I use the GUI or CLI to configure or test IP stuff.