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In this question, I learned that the "dotted-line cloud" icon in OS X's iCloud file view means "Waiting to upload". While writing a document in Byword today, I saved it and found it had been marked with this icon - there were several other documents, months old, that still had the "Waiting" icon as well.

Is there any way to, if not force, gently encourage these files to upload to iCloud?

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up vote 1 down vote accepted

I was concerned I'd have to save these documents to my local filesystem, delete them from iCloud, and then perhaps save them to iCloud over again, but it turned out that simply re-opening the "Waiting" documents, making a trivial change to them (such as deleting a character and then adding it in again), and then saving the file caused them to be synced successfully.

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I ran into a similar problem but every time I tried to open the file, the hosting application (Keynote in this case) hung. I was able to killall -9 ubd to unwedge iCloud.

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