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I am trying to upload a file larger than 4GB on a Windows server, but I can't - compare that to Google Drive which has a max upload size of 5120GB
The 4GB file size limit you're encountering is likely due to the FAT32 file system, which has a maximum file size of 4GB. However, NTFS supports much larger file sizes (up to 16 TB for Windows Server 2008 and later).
As far as Google Drive's 5120GB (5TB) limit is concerned, it is much higher because it's a cloud-based service designed for large file storage.