If you have trouble sending a message to a single contact with iMessage, the problem probably lies with them. To find out if it works for anyone, send a few messages to a few different people you know who use iMessage. Can you confirm that iMessage isn’t workin g with everyone or is it just not working when you message one contact? It is not a bad idea to examine the problem before assuming the worst. Some of the issues are minor, such as images not loading properly after iMessage idles too long on a sleeping Mac, while other issues are more serious, such as Imessage refusing to operate on the desktop. It is not uncommon for iMessage to fail, especially on the Mac. Apple’s proprietary chat platform iMessage is available on all of its devices and platforms, even the Apple watch! Apple makes this really secure, useful free service available to everyone who uses its various devices, which also supports regular text messages.
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