At an award ceremony in Oslo Norway a Microsoft programmer won the award for Most Unhelpful Error Message. Every year the Design Institute of Oslo scours the world of error messages to find the best and worst of the bunch.
This year Windows 10 update failure error message took the top place when it came to poor design. The error message seemed useful but only repeated the same information over and over, telling the user the update failed but it would try again, yet when that happened it would always fail.
This type of recursive loop is a specialty at Microsoft and the designers take pride in their ability to present what seems useful but is incredibly useless. It can take years working at Microsoft to learn from the best error message designers to make the information so sparse with information it is hard to comprehend.
I work as an engineer in Milwaukee. Currently I work on a few different UWP apps primarily Ink Calendar.