Table of Contents is not updating when upload the application.

We created a new table of contents and then we created new output (frameless) and generate a new Robohelp file. After generating the new Robohelp file, as a developer when we were updaing the new Robohelp file in the application; it didnt update, the application was running with the old robohelp file. I need to know, why the new Robohelp file is not updating the in the application?