A friend worked for a regional bank that had a strategy of purposeful obsolescence to maintain control with the core shareholders, who were mostly from one family. They were using 1980s era AS/400 systems with terminals as late as 2008, and had only 1 PC assigned to a manager in the branches, with connectivity via ISDN.
I don't know how much of this got sent out of Marsh and up to Sun though.
I've seen people waste millions on magical systems that did very little out of inertia. In one case, a system with something $10M in annual costs that managed terminal (as in VT-102 terminal) and line printer assignments. A decade after the printers were trashed and terminals moved to a (almost equally offensive) very expensive web-based system.