To add to the above, it would potentially also be useful to be able to share files based on a file tag when initially linking the Work Items. I.e you would be able to select one or more file tags from a dropdown when linking the Work Items and anything tagged with those specific file tags, would be shared and all the other files would remain unshared.

A good use case for this would be if a Work Item was regarding two separate pieces of work (say a Claim and a New Business Application), you may want to create a Linked Work Item for the Claims team and only share across the files relating to the Claim.

As well, further to Amber's above points, it would be useful to be able to see which files have been shared to the Linked Work Item (similar to emails), that way it is easier to see if any, that should have been, haven't been shared.