Adobe / SharePoint integration Checkout prompt missing

Hello,

We have found that clicking on a document in SharePoint correctly brings up the document check out prompt, however clicking on a hyperlink in a document or email to open a PDF in Adobe does not.This was working before in a previous version of Adobe. Instead now opening a PDF through a hyperlink does not save back to SharePoint at all so it seems the integration is gone when used this. 

We are now using Adobe Reader 2019.021.20058. Is there any configuration around this that we are missing?

Appreciate the help,

Tony