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.
We were producing our own TIFF files using our own software that drove monster Kodak ImageLink scanners (software I in fact took over, redid the SCSI driver of, and eventually did a clean rewrite of the engine on Sun workstations), so the images and their compression came straight from Kodak, and going further, I don't recall those 600 pound beasts ever screwing up at that level.
And this was way before Windows 98, it was Windows 3.0 or by then 3.1, like in 1992, Windows was utterly naive about document image files. Which I can see was a blessing (although maybe it was losing quality, I'd long switched to NT by the time 98 came out).
I didn't mean it was definitely the same company, just a similarly annoying TIFF issue.
So they had a wonderful core which was wrapped in baroque APIs, but the real problem was that core wasn't entirely wonderful, occasionally when you presented it a "Death TIFF" as we called the images for their file type, it would reliably crash. Software or firmware versions of the code (they had a hardware accelerated box with one or more Intel RISC chips), on the PC platform at least, e.g. Windows 3.x using a DOS box, this would entirely lock up the machine.
To get around this for a client that had 500,000 images to OCR on a tight deadline for a legal case (and this was the golden area of legal document imaging, back then lawyers would pay 50 cents per OCRed page, because a full text search could e.g. impeach a witness on the stand in real time), I created a system where the PC would always be printing out asterisks if it was OCRing pages. That allowed an operator to tour the machines and easily see when he had to manually reboot one stuck on a Death TIFF, after which my software would recognize what had happened and continue with the next image.