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OS X - Operating System General OS operation information and support

Mac dial in to Windows RRAS tips

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For those out there experiencing problems with this, trying to connect a Mac running any OS X version to a Windows Server running RRAS, I have some info that may be of help.

I noted online that Mac's prefer to use standard CHAP (MD5) encryption, while CHAP is not enabled on Windows Servers by default. So... I had to get access to the administrator of my Windows Server and ask them to enable the checkbox under Properties of Routing and Remote Access for CHAP. By default Msft selects MS-CHAP authentication, which is different.

Additionally, my Windows dial-in account had to have "passwords stored using reversible encryption" enabled in "Active Directory Users and Computers." Then the password must be manually reset, on either the client or server, n order to store it in Windows using reversible encryption.

Finally, back in Routing and Remote Access on the Windows Server, a Remote Access Policy must be created to "Grant remote access permission" for clients using CHAP authentication for NAS-Port-Type Async (Modem), done through the "Policy conditions" properties window for Remote Access Policies, which is part of Routing and Remote Access on the Windows Server.

Then from your Mac, connect using using DOMAIN\username format, with your password and the correct phone number. After much trial and error and research this finally worked and all of our OS X clients are now able to connect to the Windows RRAS. Whew! Good luck. Chad
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Very interesting! Glad you found a solution!
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