Outlook 2010 error: An encrypted connection to your mail server is not available.

Trying to setup workstation to connect to an Exchange 2010 server remotely using outlook anywhere. During the configuring email server settings, I get the following error:

“An encrypted connection to your mail server is not available.  click Next to attempt using an unencrypted connection”

I know that it isn’t the server or the user because I was able to setup an outlook profile on a different computer on the same network.  I have tried reinstalling Outlook, removed the smart card capabilities(longshot), tried manually configuring and making sure my proxy was set but I’m not able to authenticate.

Turns out that I wasn’t setting up the proxy setting correctly after all.  I went into manual config and set my proxy server and made sure that the authentication settings were set to “Basic Authentication” instead of NTLM.  Normally, that get’s setup automatically but on this workstation it wasn’t.

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