I have a linux host with openssh that permits users to login with public key.

AuthenticationMethods publickey

But now I have some users who will need to access the host as a file drop using sftp. In addition, these users will user passwords rather than key pairs.

I make all of these users belong to the group sftp_users.

an_sftp_user@myhost.example.com:~$ id
uid=1005(an_sftp_user) gid=1007(an_sftp_user) groups=1007(an_sftp_user),1006(sftp_users)
an_sftp_user@myhost.example.com:~$ groups
an_sftp_user sftp_users

Now I create the file /etc/ssh/sshd_config.d/sftp_users.conf owned by root, 0644:

Match Group sftp_users
  X11Forwarding no
  AllowTcpForwarding no
  AuthorizedKeysCommand /bin/true
  AuthenticationMethods keyboard-interactive
  PasswordAuthentication yes
  ChrootDirectory /sftp-incoming

What I want this to do is to permit users in the group sftp_users to be able to connect with password and access /sftp-incoming.

What actually happens is that I see a message server side in auth.log that says merely that the connection was closed and, client side, I see (using sftp -v) that it tries the certificates it finds in $HOME/.ssh (I've disabled my ssh-agent for these tests) but never tries password login.

Indeed, one line is this:

debug1: Authentications that can continue: publickey

So somehow my Match is not being satisfied or not being seen. But I'm unclear why.

Any suggestions where I've gone wrong?


The solution from @Gogowitsch largely answers this, especially the note that sftp-internal is, well, internal to openssh and so doesn't need a binary to be available in my chroot jail. Also important was to discover that chroot requires that the chain of directories be 0755 root all the way down, so I had to sort some permissions.

His suggestion to put the config all in the one sshd_config file was also helpful. Indeed, once it was working, moving that block back to a config file and using Include to include it fails without error. The block simply isn't used. I'm using 8.2:

OpenSSH_8.2p1 Ubuntu-4ubuntu0.1, OpenSSL 1.1.1f  31 Mar 2020

which claims to support Include (present since 7.3p1 and apparently committed on 1 Feb 2020 (prior to 31 Mar 2020).

  • Idea: You could use a second SSH daemon running on the same host, but with a different port. One allows password-based login, the other doesn't. Then tell each user which port they should used based on their preferred authentication method.
    – Gogowitsch
    Feb 25 '21 at 20:59

I see these immediate issues:

  • The order of directives. Try putting the Match Group sftp_users at the very end of the file /etc/ssh/sshd_server instead of a file in the sshd_server.d. This is because the last AuthenticationMethods seems to win.
  • The AuthenticationMethods should contain password. This is apparently what allows the password login.
  • When using the ChrootDirectory directive, you also have to use the following line within your Match Group sftp_users block:
    ForceCommand internal-sftp
    This is because the /sftp-incoming becomes the actual root of the file system to all commands. By default, the SSH server attempts to run a binary such as /usr/lib/openssh/sftp-server. From the perspective of the chroot'ed filesystem, there probably isn't any such file.

Potentially, you'll also have to run the following command to make sure that the /sftp-incoming directory cannot be accessed by 'other' (the last digit in the octal 0750):

chmod 0750 /sftp-incoming

As an experimental setup, I used the following Dockerfile:

FROM ubuntu

RUN apt-get update && \
    apt-get install -yq openssh-sftp-server openssh-server

# Create two users, first has no password, second has the password "1".
# This will also create the home directory for the sftp user.
RUN echo | adduser only-passwordless-user && \
    echo | adduser only-with-password-user --home /sftp-incoming/only-with-password-user && \
    echo only-with-password-user:1 | chpasswd && \
    addgroup sftp_users && \
    adduser only-with-password-user sftp_users

# These are needed so that sshd is happy. Otherwise,
# it likes to say “bad ownership or modes for chroot directory”
RUN mkdir -p -m0755 /var/run/sshd && \
    chown root:root /sftp-incoming && \
    chmod 0750 /sftp-incoming

RUN echo AuthenticationMethods publickey >> /etc/ssh/sshd_config && \
    printf "Match Group sftp_users                                \n\
            ForceCommand internal-sftp                            \n\
            X11Forwarding no                                      \n\
            AllowTcpForwarding no                                 \n\
            AuthorizedKeysCommand /bin/true                       \n\
            AuthenticationMethods keyboard-interactive password   \n\
            PasswordAuthentication yes                            \n\
            ChrootDirectory /sftp-incoming                        \n\
           " >> /etc/ssh/sshd_config  # cannot be ".d/sftp_users.conf"

# Start a single-connection debug server.
# Remove the -d parameter to make it long-lived but quiet.
ENTRYPOINT /usr/sbin/sshd -d

You can start a sshd running on port 2200 using this command:

docker build . -t ssh-test && docker run -it --name ssh-test -p2200:22 --rm ssh-test bash

To connect to it using sftp, run this:

sshpass -p1 sftp -P 2200 only-with-password-user@
  • Thanks, that largely got me out of this. The odd thing is that putting the (revised) block in sshd_config works, but using Include does not.
    – jma
    Feb 26 '21 at 20:30

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