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Applying Document Level Security in Workflow

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I have documents in a document set that security is applied through the Nintex workflow based on the content type (e.g. content type A is opened to security group 1 and 2, content type B is opened to security group 1 and 3).  The security workflows (applies the permissions) is run every time the document is updated (and of course when it is created).

The workflow seems to run fine the first time however when it runs again certain permissions are not applied and the users think the document is deleted/gone as no one besides admins can view it.  We have some sensitive information on our SP site so really need the security working.

What are we possibly doing wrong?  Is the problem because we are applying permissions on a document level within a document set?  Why does it seem to work one time and then lose security on the next update?

Any help here is greatly appreciated.

Corey


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