If you are being prompted for a password by outlook web app or CompanyWeb Internal Site after logging into remote web workplace. This will also give you an access denied message if you try to use the remote desktop computers link on remote web workplace.
You should check the SBS console, chance are there is a mismatch between the domain your server thinks is the external domain and the actual one. The SSL certificate may not match either.
Open the SBS console, click the network tab, click the connectivity tab.
Re-run the Internet Domain name wizard, make sure you click the adavanced button if your external subdomain or ssl certificate is not for remote.domain.com.
Re-select the trusted certificate as the primary certificate as the server will issue a new self signed cert.