I actually bumped up against legacy time/date issues while working on SSL cert parsing. An old Perl interpreter's 32-bit limits kept resetting my dates! Rather than upgrade perl or my architecture, I wrote my own perl methods to calculate infinite time (sorta?) on 32-bit systems with old perls.
For those that haven't worked with date parsing before: timezones are surprisingly complex, leap years are stupid, daylight savings is really stupid, and leap seconds are impossible without a regularly updated leap second database (similar to timezones, but worse). (The math to calculate dates correctly is rather simple, but you need to be pretty good at math to optimize it) https://github.com/psypete/public-bin/blob/public-bin/src/ne...