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I'm currently running a test Sharepoint 2013 server. Not all users are within the internal network. They can bypass the self signed cert warning for Sharepoint easily but the Office Web Apps cert warning is not as easy to bypass.

Is there a Windows/Apple utility, I can send them to add the certs to their Trusted Root Certificate Store?

There is a batch script solution for Windows: https://stackoverflow.com/a/19392938

MasterJohn
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You can actually deploy your certificate via GPO

https://technet.microsoft.com/en-us/library/cc770315(v=ws.10).aspx

I don't know how a self-signed certificate behaves with a internal SharePoint Server. In my company, we connect to SharePoint Online Services via SSO. To achieve that we needed a Certificate signed by a trusted Company like GoDaddy or GeoTrust. Maybe you also Need to take a look at this.

SimonS
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  • Thank you for information. I started to write the script for the external users to run on their own computers as admin but due to time requirements, I just heeded your advice and got a cert signed by a trusted company. I used StartSSL. – MasterJohn Oct 16 '15 at 01:39