We had a similar issue back in the 2000's, not the Y2K problem, rather file accesses.

One project I did in 2000 was porting HP-UX software to handle 64 bit file offsets, as it was originally written with 32 bit machines in mind, and the deployment scenario naturally evolved.

In Linux, I recall the whole Large File Support saga dragging on into the 2.4 era. It certainly wasn't universal until well after 2 GB devices had become commonplace even in consumer-level hardware, meaning that things like creating a whole disk image were impossible for several years.

There were a bunch of similar problems with hardware device support at around the same time - various BIOS, MBR, and partition size limits affecting 512 GB, 2 GB, and 4 GB disks (I think - my memory is pretty hazy).

Even further back, there was the infamous 32 MB partition limit in DOS 3.3 and earlier, which was still being sold with new machines at a time when 40 MB disks had become standard. Pretty much everyone in the late 80s had an awkward 8 MB D: drive hanging around as a result.

By those standards, the Y2038 problem has been handled ridiculously far in advance!

There are undoubtedly still issues in legacy apps around Y2036/Y2038 waiting to bite us, and further ahead there's likely to be some hangover in 2060/70 from the hacks put in place to deal with the Y2K issue. We might see a small army of centenarian COBOL programmers being paid very handsomely indeed...