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 If you see the warning, you should be able to click "send using NIP 44" and have it work. Support for nip 44 is not everywhere yet, but is slowly being rolled out to signers and extensions. 
 Appreciate the reply.
I only see the warning, and if I click "Click Here" it just has a pop-up explaining NIP44, but no toggle.
See below.
https://image.nostr.build/6d44e9f05709ad9ebc3ccec18bce6927896ef4203b6af3b5fe819535734dbb87.jpg 
 Figured it out!
I was logging in with an extension, so mainly just pub key was used with signing done on a per-need basis. 
Once I logged in with private testing key, I was able to test Nip-44 DMing.

Would it make sense for Coracle's messaging to request the private key specifically for this purpose? I thought the "Decrypt messages from peers" permission that nos2x-fox asks for would be included, but seems it's not. 
 Newer versions of nos2x will/do have support for NIP 44, I'm not sure if it's released yet. I don't request the private key because that's poor security practice. So right not it's all a little wonky, but hopefully will be resolved soon. 
 Nsec.app now supports Nip44, and it works with Coracle, you can try it instead of the extension.