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Reviewing through your description it appears you are running into an issue being tracked as CLOUD-1294. Looking through the bug's notes, this issue is presently in an open unresolved status, however there are a couple of workarounds available
1). Drag and Drop 1 file. Publish.
2). Use the "Click to Select Files"->Select Desired files. Publish
Additionally, if you would like to track this issue and receive updates on its status, please submit a case in your customer group here in the Jive Community and a member of our support team can associate your instance with the bug and provide you an update once the issue is resolved.