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Using a Mac OS X Yosemite 10.10.1 and Microsoft Office for Mac 2011 14.4.7 connection to SharePoint 2013 build 15.0.4667.1000 utilizing the "Document Connection" app that comes with Office 2011 shows error, "The connection failed." Cannot check documents in our out nor save them.

Document Connection does not prompt for credentials upon entering SharePoint URL. Also tried basic authentication under Preferences.

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I had the same issue. It was resolved by enabling the TLS_RSA_WITH_3DES_EDE_CBC_SHA cipher on the SharePoint Web Front End servers.

Office 2011 does support TLS 1.0 (no higher). However the server must support a compatible cipher for Office 2011 to successfully connect. The strongest cipher currently supported by Office 2011 is TLS_RSA_WITH_3DES_EDE_CBC_SHA.

I was able to determine Office 2011's supported Protocols and Ciphers by loading SSL Labs client test page in word 2011. File > Open Url... https://www.ssllabs.com/ssltest/viewMyClient.html

I originally detailed all my findings on the forum thread linked below.

http://answers.microsoft.com/en-us/mac/forum/macoffice2011-macother/document-connection-and-sharepoint-sharepoint-not/c876fcde-3d4c-4353-b4f4-35970f3a4915?rtAction=1425468285376

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The issue appears to reside in the implementation of security patches to the SharePoint servers related to US-Cert bulletin TA14-290A (POODLE). Looks like Office 2011 for Mac does not support TLS 1.0 or higher.

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