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Question: Messages stopped working since Sierra Upgrade

Since upgrade to Sierra messages has stopped working.

I get this message window:

User uploaded file

I have restarted both devices a number of times and unset and reset the neccessary messages settings.

It does occasionally seem to work sometimes but not all the time.

Any ideas?

MacBook Pro (Retina, 15-inch, Late 2013), macOS High Sierra (10.13.1), iPhone 7 running 11.1.1

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Question: Messages stopped working since Sierra Upgrade