Outlook Addin - Update Share Experation date when file updated

If I use the Outlook Add-in to Upload and Share a file, it does a great job of uploading the file and creating the share automatically with the default expiration date (15 days in our case).

However, if I make changes to that file locally, and "Upload and Share" it again from Outlook, the file itself will update, but the Share will remain the same, including the previous expiration. It would be nice if the share expiration would automatically be extended by the default expiration date when overwriting a file. It would also be nice if there was a prompt letting the user know they were overwriting a files.