So I have run into an annoyance with iMessage on my mac that's running OS Sierra. When I launch the iMessage app, I delete all the messages. I then go into the library folder in the finder, navigate to the "messages" folder and I delete the contents of the folder and empty the trash. So this should delete everything. However, if I open spotlight search and search something, old iMessage conversations appear. If I tap on a conversation from spotlight search, it will launch the chat transcript. Keep in mind, these are OLD - over 6 months old. So how can I properly delete the iMessage history on my mac, so that once deleted none appear in spotlight search?