This should be configurable to be applied by group or user. I will add another Jira item to make archiving configurable by group or user as well, as they kind of go hand-in-hand.

We would also use this for a confidentiality message as well as a "this chat may be recorded" message.

This will keep us from using Openfire if we can't add this feature. The current system we are using that we are trying to get rid of does this. It will send a message to sender and receiver at the beginning of a conversation. It should be a setting whether one or both sides receive the disclaimer.

adding a disclaimer to the start of every external conversation would be a very desirable feature (if not absolutely essential for corporate use!).

That... is a bloody clever way of handling the issue and I had not thought of doing it that way. I think that's the way to tackle it overall.