tldr: It wasn't that they couldn't keep up with the times, it's that they didn't, because they were milking their cash cow hard and wilfully ignoring the future

tldr: It wasn't that they couldn't keep up with the times, it's that they didn't, because they were milking their cash cow hard and wilfully ignoring the future. Quark committed suicide: they outsourced virtually all of their R&D, leaving none of the people who had built the previous versions employed. They ignored their users, assuming they were captive, for more than a decade. They also ignored the move to OS X for literally years, leaving (mainly Mac-based) users to choose between staying on OS 9 and moving to Windows and buying all new hardware. Adobe came along at just the right moment with InDesign -- ran on OS X, best-of-class print tools -- and you could almost hear the stampede. A real pity, too, as InDesign has a horrorshow UI, while XPress's "make boxes, put things in them" metaphor is exactly how DTP should be done.