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Accepted Answer
I know that your question was relating to Samba specifically, but you mentioned you were just getting started - so was there a specific reason to use that method for transferring files?
If not, then I’d recommend instead using WinSCP to transfer files to your server as that will still allow you the same drag-and-drop mechanism but instead it will use SCP/SFTP to transfer files to the server which will provide you better performance and security as the transfer would utilise an SSH connection instead and requires no additional setup (just provide the server IP, username and password or SSH private key).