* This release deprecates the sshd_config UsePrivilegeSeparation
  option, thereby making privilege separation mandatory.

This has (probably not wholly intended) consequences when running sshd in single user (non root) mode:

$ /usr/sbin/sshd -D -f ~/.ssh/sshd_config
Privilege separation user sshd does not exist

The problem is not limited to Cygwin, but is unlikely to happen in a typical Unix, since ssh is probably installed globally.

If Cygwin was installed without administrative privileges, creating a dedicated sshd user would be impossible (and makes little sense if sshd runs in single user mode, anyway). I guess it would be possible to add a fake user account in /etc/passwd.

Since user sshd and chroot /var/empty are not used in single user mode, it might be better to remove the check in this case:

=== cut after ===
diff --git a/sshd.c b/sshd.c
index 010a2c3..4f9b2c8 100644
--- a/sshd.c
+++ b/sshd.c
@@ -1641,7 +1641,8 @@ main(int ac, char **av)

        /* Store privilege separation user for later use if required. */
        if ((privsep_pw = getpwnam(SSH_PRIVSEP_USER)) == NULL) {
-               if (use_privsep || options.kerberos_authentication)
+               if ((use_privsep || options.kerberos_authentication)
+                   && (getuid() == 0 || geteuid() == 0))
                        fatal("Privilege separation user %s does not exist",
                            SSH_PRIVSEP_USER);
        } else {
@@ -1767,7 +1768,7 @@ main(int ac, char **av)
                    key_type(key));
        }

-       if (use_privsep) {
+       if (use_privsep && (getuid() == 0 || geteuid() == 0)) {
                struct stat st;

                if ((stat(_PATH_PRIVSEP_CHROOT_DIR, &st) == -1) ||
=== cut before ===

Best regards,

                -- Lionel

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