Hi Leee
I ran a diff on /usr/local/etc/ssh/sshd_config.orig between TC13 and TC14:
rich@tcbox:~$ diff -u open13/usr/local/etc/ssh/sshd_config.orig open14/usr/local/etc/ssh/sshd_config.orig
--- open13/usr/local/etc/ssh/sshd_config.orig 2021-03-03 15:20:54.000000000 +0100
+++ open14/usr/local/etc/ssh/sshd_config.orig 2023-04-04 14:27:09.000000000 +0200
@@ -1,4 +1,4 @@
-# $OpenBSD: sshd_config,v 1.103 2018/04/09 20:41:22 tj Exp $
+# $OpenBSD: sshd_config,v 1.104 2021/07/02 05:11:21 dtucker Exp $
# This is the sshd server system-wide configuration file. See
# sshd_config(5) for more information.
@@ -58,7 +58,7 @@
#PermitEmptyPasswords no
# Change to no to disable s/key passwords
-#ChallengeResponseAuthentication yes
+#KbdInteractiveAuthentication yes
# Kerberos options
#KerberosAuthentication no
@@ -72,13 +72,13 @@
# Set this to 'yes' to enable PAM authentication, account processing,
# and session processing. If this is enabled, PAM authentication will
-# be allowed through the ChallengeResponseAuthentication and
+# be allowed through the KbdInteractiveAuthentication and
# PasswordAuthentication. Depending on your PAM configuration,
-# PAM authentication via ChallengeResponseAuthentication may bypass
-# the setting of "PermitRootLogin without-password".
+# PAM authentication via KbdInteractiveAuthentication may bypass
+# the setting of "PermitRootLogin prohibit-password".
# If you just want the PAM account and session checks to run without
# PAM authentication, then enable this but set PasswordAuthentication
-# and ChallengeResponseAuthentication to 'no'.
+# and KbdInteractiveAuthentication to 'no'.
#UsePAM no
#AllowAgentForwarding yes
It appears ChallengeResponseAuthentication
was replaced with KbdInteractiveAuthentication.
I'm guessing TC14 is failing because KbdInteractiveAuthentication
is not defined because you are restoring the TC13 version of
/usr/local/etc/ssh/sshd_config.
Adding the KbdInteractiveAuthentication variable to your TC13
backup of /usr/local/etc/ssh/sshd_config might allow it to work
for TC13 and TC14.