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I've been using an older version of the server for way longer than I should, and finally decided to update. I took note of all my previous settings, but the version I'm using now looks so different that I might be missing something.
When trying to connect as a user from a remote machine now, I get the following:

Status: Connecting to (MY IP HERE)...
Status: Connection established, waiting for welcome message...
Status: Initializing TLS...
Status: Verifying certificate...
Status: TLS connection established.
Status: Logged in
Status: Retrieving directory listing...
Command: PWD
Response: 257 "/" is current directory.
Command: TYPE I
Response: 200 Type set to I
Command: PASV
Response: 227 Entering Passive Mode (MY IP HERE)
Command: MLSD
Response: 150 About to start data transfer.
Error: Connection timed out after 20 seconds of inactivity
Error: Failed to retrieve directory listing



On the server side, Everything looks good until here:

<< [FTP Session 15 CLIENTIPHERE Chris] 150 About to start data transfer.

DD [FTP Session 15 CLIENTIPHERE Chris] tls_layer_impl::on_read()

DD [FTP Session 15 CLIENTIPHERE Chris] tls_layer_impl::failure(-110)

!! [FTP Session 15 CLIENTIPHERE Chris] GnuTLS error -110 in gnutls_record_recv: The TLS connection was non-properly terminated.


Any pointers would be amazing or additional info I need to provide just let me know.
Thanks in advance!

Double check your PASV settings, making sure the server is able to report the correct IP to the client and that the ports range is the one you expect.

Then make sure your firewall rules, if any, allow the server to make use of those ports. Also make sure that your router, if any, is forwarding those ports.

Wow, I'm an idiot.
Just had to re-add it in windows firewall -_-
Thanks for the help