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I know that most enter­prise soft­ware pack­ages have shock­ingly, egre­giously bad user expe­ri­ences. One of the most tor­tu­ous aspects of the com­mon inex­cus­ably bad enter­prise soft­ware pack­age user expe­ri­ence is the stun­ningly use­less, hos­tile, and cryp­tic error mes­sages these mon­strosi­ties return when­ever users have the mis­for­tune to step out­side the bounds of their opaque, byzan­tine oper­at­ing logic.
Here’s a tasty exam­ple of the genre from an imple­men­ta­tion of Peo­ple­soft, that leaves me feel­ing like I’ve been barfed on by a machine.
Peo­ple­Soft Error:

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