In my experience Ye Olde Web App backend services tend to be particularly bad with time because so much is generally done in the request/response model.

For business-logic reasons, where I've generally seen it fall apart is when things go from fairly simple things like "after six months of inactivity this account is considered idle" to more complex interactions of timers and activity types. "Move fast and break things", "just get to MVP" attitudes rarely have the discipline to formally draw all the distinct states out as the number of potential states starts to exceed a couple dozen.