1. Is ASP.net service started?
2. Do you have access to hit https://mysoftware.passageways.com from the server where Expressway is installed?
3. Are all required roles and features installed?
4. What does the RAP log file say is the issue? Located here- Drive:\programdata\Passageways\RAP\Log file with date and time of install/update attempt
5. Make sure Windows Installer service is started.
6. Make sure you username and password are correct!! Log in to https://mysoftware.passageways.com and then copy/paste the password to ensure you're correctly typing it in.
7. Does another user's login credentials work?
8. Try logging in with a local server account