Systems and methods support secure transfer of data between workspaces operating on an IHS (Information Handling System). Upon a request for access to a first managed resource, such as protected data, a first workspace is deployed according to a first workspace definition. Upon a request for access to a second managed resource, a second workspace is deployed according to a second workspace definition. In response to an indication of a portion of the protected data from the first workspace being copied to a buffer supported by the IHS and of a request to paste the copied portion of the protected data to the second workspace, the protections provided by the second workspace are evaluated. If the protections of the second workspace are inadequate, an updated second workspace definition is selected that specifies additional protections. The second workspace is updated according to the updated second workspace definition and the transfer is permitted.