This problem has been solved.

The problem was that the Windows SSH Server had reverse DNS lookup
checks turned on, and I had no reverse lookup DNS entry for the test
server (FreeBSD), but did have one for the working server (Linux).

It had nothing to do w/ the OS or OpenSSH version.

-DW


Duane Winner wrote:
> Hello,
>
> I have a business client who is running a SSH Communications SSH
> Tectia Server on a Windows NT Server.
>
> I need to connect to their server from dozens of FreeBSD servers in my
> organization using OpenSSH client, using publickey auth only.
>
> During testing, after entering the passphrase for private key, I am
> being prompted for a password, which has never happened to me before
> when connecting openssh->openssh.
>
> He claimed that he tested on his side, and was able to connect from a
> Linux client to his own Windows Tectia SSH box.
>
> So I copied my private key to an old Linux box, and tried that -- it
> worked as he claimed.
>
> Why does openssh client behave differently between Linux and FreeBSD?
>
> Or is it an issue with the versions of OpenSSH, and something changed?
>
> Is there an option I can pass on my FreeBSD box to get my OpenSSH
> client to work as it does on the Linux box?
>
> FreeBSD Client (cannot connect to server):
> FreeBSD 5.5-RELEASE-p8
> OpenSSH_3.8.1p1 FreeBSD-20060930, OpenSSL 0.9.7e-p1 25 Oct 2004
>
>
> Linux Client (can connect to server):
> Red Hat Linux 7.2 2.96-118.7.2) Red Hat 2.4.9-e.27smp
> OpenSSH_3.1p1, SSH protocols 1.5/2.0, OpenSSL 0x0090602f
>
>
> Windows Server:
> Remote protocol version 2.0, remote software version 3.2.9 SSH Secure
> Shell Windows NT Server
>
>
> Command on both FreeBSD and Linux Clients (again, works on Linux,
> fails on FreeBSD):
> # sftp -vvv -o IdentityFile=.ssh/testuserkey testuser@192.168.0.100
>
> ---------------------------------------------------------------------------------
>
> Logging on Linux:
>
> Enter passphrase for key '.ssh/testuserkey':
> debug1: read PEM private key done: type RSA
> debug3: sign_and_send_pubkey
> debug2: we sent a publickey packet, wait for reply
> debug1: ssh-userauth2 successful: method publickey
>
> and then I'm in.
>
> ---------------------------------------------------------------------------------
>
> Logging on FreeBSD (notice that I never get a reply from the server as
> I do when connecting from the Linux box. Why is this?):
>
> Enter passphrase for key '.ssh/testuserkey':
> debug1: read PEM private key done: type RSA
> debug3: sign_and_send_pubkey
> debug2: we sent a publickey packet, wait for reply
> debug1: Authentications that can continue:
> debug3: start over, passed a different list
> publickey,keyboard-interactive
> debug3: preferred publickey,keyboard-interactive
> debug3: authmethod_lookup publickey
> debug3: remaining preferred: keyboard-interactive
> debug3: authmethod_is_enabled publickey
> debug1: Next authentication method: publickey
> debug2: we did not send a packet, disable method
> debug3: authmethod_lookup keyboard-interactive
> debug3: remaining preferred:
> debug3: authmethod_is_enabled keyboard-interactive
> debug1: Next authentication method: keyboard-interactive
> debug2: userauth_kbdint
> debug2: we sent a keyboard-interactive packet, wait for reply
> debug1: Authentications that can continue:
> debug3: userauth_kbdint: disable: no info_req_seen
> debug2: we did not send a packet, disable method
> debug1: No more authentication methods to try.
> Permission denied ().
>
>
> Thanks for any help with this that anybody can provide!
>
> -DW
>