Microsoft Windows (bugs relating to icons "down at the clock" and tooltips of those icons, sound volume management, start menu lag, stupid search in start menu, where when you type 3 letters it finds the thing you search, but when you type 4 letters it is no longer there, worse and worse system settings dialogs, hiding everything behind 3 more dialogs to click, and many more)
Salesforce Slack (buggy Markdown parser (what is it with these big companies always getting something like Markdown wrong???), laggy as hell, still no voice chat on FF, ...)
All of these big companies make dysfunctional software, that they can only push down our throats, because of uninformed management levels and the sheer size of marketing budgets they spent.
We probably got a feature complete/working within less than a week then spent months as the CEO (who was a product guy) was nitpicking. We'd routinely throw away features if we felt they didn't fit well.
In the end it didn't really matter. I liked the tool and was proud of it, but it in terms of making money, it didn't do well.
In their defence who wants to be the first PO to ship nothing for extended period of time. Long term always takes a back seat to short term, IMO in any company pressure must come from the very top
But I think the main factor is that it's not-business software by a relatively popular (and well-liked) "small" software company.
I would say that software should be first smart, then it can be fun.
EDIT:
In a user's guide I introduced diagrams of calculations with points for scalar values, vertical bars for vectors, and then square 2-D grids to represent matrices, which I referred to as "waffles". With "waffle", referenced by page, in the index at the back of the guide.
I wondered if anyone would register the mild ridiculousness, but I had people coming up to me in conferences later laughing about matrix waffles.
It would be like putting flashing lights on a hammer every time you hit a nail. Might sell well at Christmas but very few carpenters I know would want one.
Tools should be practical, entertainment should be fun.
The Salesforce Behemoth Corporate Machine is slowly eroding the character of Slack, though, sadly.
Certain menus were not being properly translated when switching languages in the app. You know what they say about menus — they’re most helpful when you can read them.
Honestly this is the tone that should have all release notes!