iMessages won't send pictures after high sierra update
I recently updated a number of my Macs to High Sierra. One of them now won't successfully send pictures via iMessage to an iPhone. I have tried multiple iPhones with the same result. The iPhone user sees a "downloading" icon like the one pictures below, but never receives actual image. The iPhone has the latest iOS. Any suggestions?
MacBook Air (13-INCH, MID 2011)