Hello, @mickelodian

The ‘PasswordAuthentication’ can be enabled temporarily in order to add new key when the old one is lost or just when the ssh connection can not be established for some reason with the current key (although you should always first check the key’s file ownership/permissions)

You can enable PasswordAuthentication for your Droplet by modifying your /etc/ssh/sshd_config file. Once set to Yes restart the SSH service and connect via an SSH client for a more stable connection. You can then modify your ~/.ssh/authorized_keys file to add the appropriate public key.

This change can be made from DigitalOcean’s console. If you’re having issues accessing the console you can then reach to our amazing support team that can help you further with this.

To enable the PasswordAuthentication follow these steps:

1. Log in to the console on the DigitalOcean website.
2. Type sudo nano /etc/ssh/sshd_config
3. Change PasswordAuthentication from “no” to “yes” and save the file
4. Open a terminal on your computer and type ssh username@[hostname or IP address] or if on a Windows box use PuTTY for password login making sure authentication parameters aren’t pointing to a private key
5. Login with a password
6. Type sudo nano ~/.ssh/authorized_keys
7. Paste public key text here and save the file
8. Type sudo nano /etc/ssh/sshd_config
9. Change PasswordAuthentication from “yes” to “no” and save the file
10. Log out and attempt to log back in (if using PuTTY make sure you set up auth parameters to point to your private key)

You can then upload the key using this command:

ssh-copy-id -i ~/.ssh/mykey user@droplet

Hope that this helps!
Regards,
Alex

Hello,

You can double-check the configured settings in FileZilla and make sure that the ssh-key is added/present.

Configure FileZilla
After you install FileZilla, you need to configure it to connect to the Droplet.

Open FileZilla and then click Settings in the Edit drop-down menu.

In the Connection section, click SFTP. This is where you add your Droplet’s private SSH key. Click Add key file…, then locate your Droplet’s private SSH key on your local machine. If FileZilla prompts you to convert the file into a supported format, click Yes.

After you add the SSH key, open the File drop-down menu and click Site Manager. The site manager lets you add, remove, and manage servers and devices that you want to connect to using FileZilla.

Click New Site and enter the name of the Droplet. In the protocol field, select SFTP from the drop-down menu. Enter information for the following fields:

• Host: The IP address of your Droplet.
• Port: Enter the port you use to connect to the Droplet (port 22 is the default).
• Logon Type: Select Interactive.
• User: Enter the username you are connecting to the Droplet with (root is the default user on most Droplets).

Once you have entered your settings, click Connect. The status field in the top window displays the status of the connection.

You can check this article on How to Transfer Files to Droplets With FileZilla

and also this one How To Use Filezilla to Transfer and Manage Files Securely on your VPS

https://www.digitalocean.com/community/tutorials/how-to-use-filezilla-to-transfer-and-manage-files-securely-on-your-vps

https://docs.digitalocean.com/products/droplets/how-to/transfer-files/

Hope that this helps!
Regards,
Alex