Issues with Build project

For as long as Ive worked with our code base this has always been the case and recently I'm trying to see what I can do to fix the issue.

For some reason, build>build project has never worked. It begins compiling and eventually ends up with compile errors. This is the same when auto compile is enabled and trying to compile from a clean state. The workaround is users are forced to use build>rebuild project which works with no issues what so ever. There seems to be some order differences or something that causes one to succeed and the other to fail.

Im trying to figure out the root cause of why this is happening and am hoping someone can help point me in a direction. Where should I place debuggers, what should I look for, maybe Im missing some project configuration? If anyone knows what the difference between the two is that would also help.