This trophy is earned in the "Prologue" chapter but isn't actually awarded until after the "Sleazy Place" chapter finishes loading. It has very specific requirements which are not fully detailed in some guides and forums, causing it to be reported as glitchy. Because of the delay in awarding the trophy, it is important to make sure all steps are finished as each attempt takes about 20-30 minutes to completely play through to the point it is awarded.