On Amethyst, there is a little incognito icon on the text field that you use to write replies in private chat screens.

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Is there any indication that it is working on the other end? If its not enabled on the recipient's side, will communication commense using the insecure method regardless of the setting?

I answered my own question:

Old->new: new recieves, but shows with insecure icon.

New->old: old does not recieve

Make sure your relays are accepting these encrypted messages. Many of them are still unaware of the new type.