Suppose I want to upload a file to a server using regular FTP from within Whonix. Does this prevent the server owner from knowing my IP address when I upload the file? Or is it even possible to upload a file using FTP and Whonix? These are the settings I use normally to upload to this server (on Windows, when they do know my IP):
I use FTP because the server does not support SFTP or FTP with any encryption. I am not concerned with the account’s FTP credentials being stolen.
Welcome to the Whonix forum!
Short answer: yes.
For future questions that might come up: The modus operandi on here is to only ask questions or address problems related directly to Whonix itself (yours could have been asked about Tor in general too) and to make use of the existing material (e. g. the Whonix wiki), but you can read up more about that on the following page.
Also, in case it isn’t obvious, you probably don’t want to connect with the same server and credentials as you did over clearnet.
No one will know who you are unless you registered on the server without Tor at any point or use credentials unique to your non anonymous accounts.
Using Tor does not provide end to end encryption unless the endpoints are running onions. So yes your passwords will be sniffed unless the site implements FTPS.
Do I need to do anything special to ensure that my IP address stays hidden when using FTP in Whonix, or is that just a given under its default configuration?
The whole premise of Whonix is that everything is routed through the Tor network. Also File Transfer Protocol (FTP) already states that “Filezilla works out of the box.”