Me, with zero C/C++ experience, being asked to figure out why the newer version of the Linux kernel is randomly crash-panicking after getting cross-compiled for a custom hardware box.
("He's familiar with the the build-system scripts, so he can see what changed.")
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I spent weeks of testing slightly different code-versions, different compile settings, different kconfig options, knocking out particular drivers, waiting for recompiles and walking back and forth to reboot the machine, and generally puzzling over extremely obscure and shifting error traces... And guess what? The new kernel was fine.
What was not fine were some long-standing hexadecimal arguments to the hypervisor, which had been memory-corrupting a spot in all kernels we'd ever loaded. It just happened to be that the newer compiles shifted bytes around so that something very important was in the blast zone.
Anyway, that's how 3 weeks of frustrating work can turn into a 2-character change.
The original stakeholders are long gone, the system is too valuable to be replaced and each quirk handles specific cases that are not documented anywhere. Bonus point if it's in a semi-dead language like VBScript. Please fix.
We found an issue in the kernel bug tracking that seems to explain it, but we never confirmed for sure. Fortunately updating either of those things fixed the issue. This was of course also hard because this was back in the golden days of vmware managed by client's IT team, so getting them to update things on a VM was hell as well.