Q: Why does my iMessage send from my email and settings are checked correctly

Hey llallendorph,

Thanks for the question. If I understand correctly, you want to start a iMessage conversation from your phone number. I would recommend that you read this article, it may be able to help the issue.

check under Send & Receive

iOS and OS X: Link your phone number and Apple ID for use with FaceTime and iMessage - Apple Support

Thanks for using Apple Support Communities.
Have a good one