​@CorGreggB 

> How do we get the Security Checkpoints to support the On-Save Release Operation?

I think the error message is trying to convey that the two features doesn't work together. Either disable the security checkpoint we have for approving or releasing documents, or save the document, then use one of the mentioned commands.

>  Since I cannot test the On-Save Release, how do you check in a Document if the Revision is already Released?

You can't, since the document is more or less completely locked once it has been released. I frankly don't know why we have kept the "Release" under On-Save Operations. It could be that we tried to make it work like in IEE, then realized it's not possible, but forgot to remove it. I suggest you ignore it. The Status -> Quick Release commands should work fine for releasing a document revision quickly.

It should be rare, but it is allowed to release a document without a file or a registered "original" (physical documents.) What "the document content" is, in that scenario, is hard to say. Perhaps the document is just a reference to something that is stored in another system, and we want to keep information about it being released?