1) Connections hanging over a frame relay network that one day started dropping packets over a certain size. Work-around was adjusting the MTU until I was able to convince the frame relay network operator that something was broken in their network. Initially it was confusing because an interactive telnet session over the network would work fine till you did something like "ls -l" or tried to read a man page which generated enough text to send a full size packet, then the connection would hang.
2) Unable to reach a Verizon e-mail paging gateway but only when connecting from a Linux box. An OS X box on the same network as the Linux box could reach the gateway fine. Turned out Verizon had a firewall rejecting connections where the ECN bit was set. Linux was setting ECN, OS X was not.
3) Solaris box A could initiate a connection to box B, but not the other way. After A talked to B, B could then talk to A, but only for a short period. Someone had deleted A's own MAC from A's ARP table, so A wasn't replying to ARP requests for itself. But if A connected to B, B would keep A's MAC in its own table till it timed out after which B couldn't initiate connection to A any more.
4) All manner of misconfigurations over the years where you learn to recognize the symptoms: misconfigured netmask size; misconfigured duplex; duplicate IP address on same network. You rarely see these any more.
5) The infamous 500-mile e-mail. :-)
6) And my favorite - https://www.pagerduty.com/blog/the-discovery-of-apache-zooke...