The external certificate had expired and a new one had been installed but Remote Web Workplace was only responding with connection refused. I found an error in the event log that showed World Wide Web Publishing service was not started. I started the service and then when trying RWW the error was 404 not found. I opened IIS and found that the SBS Web Applications site was not started. Starting the site fixed the problem.
SBS 2008 RWW not responding
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