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Helpful answers
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Sep 22, 2016 6:51 PM in response to james charlieby Ulexes138,Hello james charlie,
Thanks for reaching out to the Apple Support Community. I know how important it is to keep your messages working as expected, and I'd like to help. If you have not already, it's always a good idea to start by restarting your device. If that doesn't work, however, I'd recommend signing to of iMessage and then back in.
You can sign out under Settings > Messages > Send & Receive. Tap on your Apple ID and select sign out.
If the behavior persists, or you run into any trouble, the entire community is here to help.
​Best Regards -
Sep 23, 2016 12:30 PM in response to Ulexes138by jd274,The last few days, I'm having the same problem. Freshly updates iPhone6 and MacBook. I've disconnect and reconnected the accounts, restarted, and cleared message histories, but regularly images are failing to send (at all) from the macbook and when they do send from either the iPhone or the MacBook, the other device flashes a "Your message could not be sent" (on Macbook) or "Not delivered" on iPhone.
Based on the timing, is it fair to assume this is the result of the the ecosystem updates, lately?
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Sep 23, 2016 8:18 PM in response to jd274by james charlie,I already fix it, it seems the problem is not on my phone, the person that I'am trying to send the pictures turned off his iMessage for a week.
