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Document Connection Check In button not available

We are using the document connector with limited success, we have no problem checking out a document and /or adding a file to our share point sites, however when we check out a document with or with out changes to the checked out document the "Check In" button is grayed out, leaving the document in the "editing" stage.  only the delete option is available, but that is not helpful when a change has been made to the document.  We are using Adobe Illustrator .ai files for the above scenario. 


MS Doc Connection for Mac 14.3.7

OSX 10.8.5


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