I&#x27;ve found upgrade hell can apply to C#&#x2F;dotnet stuff too. I work on a project that has attempted to upgrade Entity framework versions multiple times and keeps pushing it off because we get buried in compile time errors. It&#x27;s a case where Microsoft supported several different paths to architect an app and then quietly deprecated half of them - database first vs. code first, POCOs vs. ObjectContext, etc. and we happened to be on the losing side of history. Compile-time errors are definitely easier to find, but the path to fixing them can be just as bad. What I really long for is good documentation and a clear path forward for each breaking change.