freeSSHd to allow ssh connection with windows server 2008

You should have port 22 open on the firewall to allow ssh connections.  You should be using scp or sftp to connect, not ftp.  You should test winscp on the local system first to make sure you can connect winscp first.  Once that's tested, you can then try winscp from a remote system.

Yes I went through steps to open port 22 according to this picture:

I am not sure if I was successful. Maybe I need to restart iis/server? How to test.

freeSSHd should be a stand-alone server.  You don't need IIS.

You can test it by installing and running winscp on the same system you installed freeSSHd on.  Run winscp and connect to localhost on port 22

on same windows server 2008 I connect to port 22 using winscp scp

options when connecting:
copy key
ssh-rsa 1024 06:4e:c0:ca:0f:6d:0d:dd:52:86:7b:3f:a4:0f:c6:f7
then I press yes


same error happens (see previous screenshot where I connect using winscp on windows7)


now I paste on .txt, next .ppk format and upload key file

How did you generate the winscp-key.ppk file?  That's a Putty Private Key extension.  You may need to convert it with puttygen.exe

I am not a server expert.  I do not understand.  Please include tutorial of putty connecting if necessary

I copy pasted the string when winscp asked me to connect.
yes no copyPaste


when I change password, winscp alert box, 'wrong password' and I am prompted for password

so I am connected to something.

Here are some links that describe the putty key and how to generate it.

http://winscp.net/eng/docs/ui_puttygen
http://support.cdh.ucla.edu/help/132-file-transfer-protocol-ftp/583-converting-your-private-key-

http://www.howtoforge.com/ssh_key_based_logins_putty
https://www.digitalocean.com/community/articles/how-to-create-ssh-keys-with-putty-to-connect-to-a-vps

Is that the only method to test if freeSSHd is working

Can i check server side rather than client side


http://winscp.net/eng/docs/ui_puttygen
I think I got client side to work
creating private key no paraphase and loaded when I connected.
I could not see files and still have similar client side error
newest version of winscp has less error reporting
dialog box 'network error: connection to website.com refused'


but
I still do not know how to check server side
I put down two users 'j3' (exists) 'administrator' (does not exist)
I am using 'nt authentication'?

Or what step do you think I should take now to get closer to establishing ssh connection?

What other information should I provide?

May you please request the attention from experts in my previous question.
https://www.experts-exchange.com/OS/Microsoft_Operating_Systems/Server/Windows_Server_2008/Q_28394159.html
comfortjeanius suggested the link I am using in current question.
Seth Simmons stated that 3rd party tools are needed.

Dave answer worked.