So I notice that alot of times when I have a restart step in my TS, it doesn't flash the custom message I have set notifying the user, it just restarts, and sometimes won't even do that. Is it true that the restart step isn't always dependable or?

My only thought here is that its actually not the restart task causing the restart. Programs run using an Install Software task that return a 3010 error code will cause the task sequence to restart the system. This restart is pretty much instant. Without knowing more about your task sequence though, this is a total guess.Jason | http://blog.configmgrftw.com | Twitter @JasonSandys

Jason is correct in that the restarts which don't have a notification are caused by apps/programs that return the re-start code. If you want to display a notification even for such cases, what you can do is add a re-start step after each app/program. On those re-start steps, add a condition so that the step would only run if the _SMSTSLastActionRetCode variable is equal to the re-start code (3010).