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I have an iPhone with iOS 8 and a Mac with Yosemite, which means I can send SMS messages from my Mac (which I absolutely love). However there are some special cases that it doesn't handle as I would like it to.

For instance, my sister has an iPad with iMessage set up, but she uses an Android phone (i.e. no iMessage). If I try to send her a message from my Mac, it usually (not sure if always) sends to her iMessage account. This is a problem since she doesn't always have her iPad with her so sometimes she doesn't see my message for a long time. On my phone my messages with her are split into two threads, one for iMessages and one for SMS messages, so I always reply to the correct address. However, on the Mac they are merged into one thread. So sometimes she sends me a SMS from her phone, which I receive on the Mac, but when I reply it sends an iMessage.

Is there a way to either force Messages on the Mac to send to a specific address or to split the thread as it is on the iPhone?

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you can choose where your message will go: click on the little down arrow right to the recipient's name, and select the destination Message or iMessage (or even other chat system like jabber or bonjour).

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    That doesn't help. I might be sending to that person's phone number, but if they have iMessage turned off, they will not get the message. – Jowie Aug 21 '15 at 12:40
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    Only "iMessage" is available for me on Mavericks. If I can send SMS to Android devices via Mac Messages, theoretically I should also be able to do the same to iOS devices. But Messages is not providing me that option. – user166405 Oct 5 '16 at 4:02
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You can direct a message to a particular destination using the Contact Card. Right-click a conversation with your sister from the list on the left and choose "Show Contact Card" from the pop-up menu, click the label beside the entry for her Android phone (such as "Mobile" or "Work"), then select Send Message from the pop-up menu.

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    This doesn't work if you can send iMessages to that number. – Tyilo May 28 '15 at 13:01

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