Creating New OpenSSH Keys with PuTTYgen for WinSCP, Putty, or OpenSSH

Generate the original SSH private key with ssh-keygen

It is generally safer to generate your key with ssh-keygen first, and then import it into PuTTYgen for usage to generate the .ppk file. So let’s do that! By the way, this key has had information modified, and has been deleted immediately after testing. Just to let you know.

PS C:\WINDOWS\system32> ssh-keygen -t rsa
Generating public/private rsa key pair.
Enter file in which to save the key (C:\Users\test/.ssh/id_rsa): C:\id_rsa
Enter passphrase (empty for no passphrase):
Enter same passphrase again:
Your identification has been saved in C:\id_rsa
Your public key has been saved in C:\id_rsa.pub
The key fingerprint is:
SHA256:UxcPxfHY5ZDzU8i+IOCKWXArxuUC3fdtrxtAzBT/VrM user@test
The key's randomart image is:
+---[RSA 3072]----+
|   . .    o.o+++.|
|  . o + o+ . +**o|
|   o = + o=.o.o+*|
|    = + .oo.+..o+|
|   . * .S .o ooE.|
|    o .  . . .o  |
|            ..   |
|            ..   |
|            ..   |
+----[SHA256]-----+

Now open the PuTTYgen GUI Program

Now we have to generate the .ppk file using PuTTYgen. Open PuTTYgen by hitting +R on your keyboard.

Then from the PuTTYgen console click the load button. And browse for your private key file which was generated by ssh-keygen

Load your private key

Click the button that says “Load” to select your private key. Then you will be prompted to enter your password for the private key.

You may get a message box which warns you about the SSH version 2 being used for the key. Go ahead and click “OK” to close the prompt.

Save your private key as a .ppk file

Now take the putty pubkey from the PuTTYgen GUI and upload it to your host panel or place into the authorized_keys file. Likewise, this should work for Lightsail or EC2 on AWS. As long as your key is made to the standards of the AWS platform you are using.

user@server:~$ echo "ssh-rsa <public_key> user@test" >> ~/.ssh/authorized_keys

Now configure the connection with WinSCP

Go ahead and run WinSCP, either by using the run dialogue if the program is in your PATH environment variable, or open it by using the start menu.

Now click on the button that says “Advanced” to edit connection information. Then go to “SSH > Authentication” under the left panel menu. Then fill out the path for your .ppk private key. Then when you are done, click OK.

Log into the server with WinSCP

Once you have saved your .ppk file into the Authentication dialogue. Go ahead and click “Login”. If you get a warning about connecting to an unknown server and adding its host key to a cache. Go ahead and click “Accept”. Then you will be prompted for your username and password. Go ahead and enter your password for the new connection.

After you enter your password and hit enter or choosing to continue in the dialogue.

Enter your password

You should now be connected to the server via WinSCP!