I bet I worked with the same company when I was with the government. We had a subcontractor who'd been hired to digitize something like 200 million paper records (they made it about 50 million in before we ran out of funding). But a small fraction of the TIFF files they generated wouldn't work with any of the tools we had on hand.

It turned out that Windows 98 shipped with an Imaging program (Licensed by MS, not written by them) which predated the standardization of the JPEG-in-TIFF subformat, but they'd basically guessed at how it would work and shipped that. The final spec (and the version of JPEG-in-TIFF nearly everyone else implemented) ended up being different. So basically nothing could read it.

We ended up calling them up every time a customer found one of these files and having them print out that image on one of their windows 98 machines, and scan the printout back in using one of the newer machines. Sure, we lost some quality, but at least the customers could access the data now.

For a time reference, these broken images were still showing up in newly scanned documents in 2011 (when we stopped working with them due to massive fraud), so they must have been using their Win98 scanner systems even then.