Over my IT career, I've had to dig into networking-related issues far more than I would have liked. That said, some especially bad times were:
In the early to mid-90s before the networking landscape stabilized and everyone decided "TCP/IP and Ethernet-type networking are the way to go".
In the 90s, doing office LANs was a revolving cast of Banyan, NetWare, AppleTalk and others. Woe be unto you if you had to make them interoperate.
Similarly, mainframes from various manufacturers neither wanted to play nice with each other nor those new-fangled "open" systems. SNA, HIPPI etc. were all fun.
Trying to find out which host on a token-ring network had decided it wanted to just keep the token was also quite fun. There's nothing like telling everyone in an office, "everyone, yo need to shut down all your computers, printers, etc. We have to reboot every device to get everything talking, again."
LAN-to-WAN? Joy.
Getting PC-type systems to talk to Apple type systems? Joy. Fortunately(?) never had to deal with bridging the gap from AppleTalk systems to anything by PCs.
Getting PC-type systems or Apple systems to talk to "Open" (i.e., "UNIX") systems? Not usually too horrible, mostly just sorting out installing a TCP/IP stack like Trumpet WinSock for Windows systems.
Getting PC-type systems to talk to mainframes? It was usually others' repsonsibility to get the mainframes onto the TCP/IP networks. Then all the PCs needed was a 3270 emulator application ...turning the PCs into glorified dumb-terminals. The need to enable real interop was mercifully rare, but decidedly "joyful" when it was required.
More frequent than full PC/mainframe interop was "open" systems to mainframe ...and "mainframe" was a whole gallery of pain: IBM big-iron and (while not technically "mainframes, setting up interop still wasn't exactly pain-free) A/S 400s; Burroughs; Tandem; Stratus; ...the hell-list goes on.
At any rate, all of the above prose was mostly an excuse to re-share this XKCD.
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