adding versions to approvals

I'm writing complex instructions for how my staff should upload new versions into Wrike because this is a new process for them and the current process does not appear to be intuitive. 

Intuitively, my users' first thoughts when they want to add a new version to an approval from their computer is to choose the Add files link, however, once the file is added, the AI assistant tells me there isn't a way to add the most recent file as a version in the approval, although to be fair, it said you could take them out of the approval add them back in (which didn't work).

Now, if a user's first thought was to click the box of a file that was already in the task or added to the approval, they would get a nice header section with a bright Add Version button that would seem like this works very intuitively.  Alas, Add Version will only go to their computer files when clicked, causing consternation.  If there was a way that files recently uploaded to the task could be added to the approval and versioning, this would make this trial much less sad but there does not appear to be. 

I'm wondering if community members or Wrike staff might know if I'm missing something that will make this process work better without taking up a lot of real estate in the description for the process?