You can determine which address is being used for an iMessage conversation by tapping the “Details” button in the top right corner and then tapping the “i” button beside the user’s name. So an iMessage conversation with somebody’s phone number will be separated from an iMessage conversation from that person’s email address, even if both share the same contact record in your iOS address book.

The Messages app on iOS divided conversations based on the sender’s address, without regard to contact entries. So in other words, if your fiance sends you a new iMessage, it will come from the address specified in the settings above, but if he’s replying to a message you’ve recently sent, it will come from whatever address you sent that message to. As the name implies, the address selected under “Start New Conversations from” is the one used to initiate new conversations in iMessage, but there’s a catch: When replying to existing iMessage conversations, the sending address will be the same one that was recently used in that conversation.

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