Using the Upload Multiple Files feature, how many files can be uploaded to a document library at a time? Does it depends on total size of the files?
How many files can be uploaded to a SharePoint Document Library at a time?
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It depends which 'uploader' you are using. Microsoft has changed this at some stage with a service pack.
The 'drag and drop' uploader maxes out at 100 files (without giving a decent message). The 'Treeview' based uploader does not have a limit I believe, but has other annoying limitations.
(Copy from my answer on the same question on SharePoint Overflow)
As I know, there is only restriction on maximum document size (default is 50MB). You can configure it in Central Administration -> Web Application General Settings page. I don't think there are restrictions on maximum files uploaded at one time.