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If you're not a group owner, ask your group owner to turn the feature on.
Group Owners
Refer the Group Options and Settings page within the KB.
Can you upload multiple files at the same time?
Yes, from your desktop, drag and drop the files you wish to upload. You may wish to move these files to corresponding folders. Be certain the content matches the folders you desire.
Yes. Files and folders can be shared across Groups you have permissions for.
Check to see if the files are shared. You may have two different documents with the same name. Check to see if the Media Gallery contents were posted twice.
Ask the Group Owner if the content is being pulled from another location? You will need to have permissions in both locations to see the content.