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Reply to iCloud for Mac is stuck on "waiting to upload"
I have the exact same situation: iCloud with sync for my Desktop/Document folders and regular git usage. The upload is stuck. I called Apple Support. First stop was iCloud support, who said it seems to be a MacOS issue. I was forwarded to MacOS support, who said that it needs to be upgraded. I got Andrew, a senior support person in MacOS, who spent 3 hours with me, gathering various diagnostic information. He will be upgrading it to the engineering team. I will update what happens after talking to them.
Jul ’20