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High Sierra: "Messages" sends everything *except* images

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Joined
Mar 10, 2014
Messages
47
Motherboard
Asus Z97-P
CPU
i3-4360
Graphics
710
Mobile Phone
  1. Android
  2. iOS
High Sierra is working flawlessly on my Asus Z97-P + G3258... except "Messages" sends everything *except* images. I can receive images, but not send them. I've logged out/in of my iCloud account, rebooted a few times, but to no avail.

Would someone be able to help me, please?

Thank you, have a wonderful day :)
 
High Sierra is working flawlessly on my Asus Z97-P + G3258... except "Messages" sends everything *except* images. I can receive images, but not send them. I've logged out/in of my iCloud account, rebooted a few times, but to no avail.

Would someone be able to help me, please?

Thank you, have a wonderful day :)
Are you able to add the image to the message but it just won't send?
 
Yes, that's correct.

Additionally, I disconnected my ethernet from the machine, and connected to a mobile hotspot, to eliminate the router being the cause of the issue; the issue remains.

More weirdness:


If I send myself an image on my iPod, it shows sent/received on iPod AND Mac… and if I drag the image I received from iPod, off Mac Messages to the Desktop, and then drag it back into the message box and send… IT SENDS!
 

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Could it be the format? I'm just guessing b/c I have no idea what it could be except for that. Real strange.
 
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