diff --git a/security/openssh-portable/Makefile b/security/openssh-portable/Makefile
index 69edba17e8cc..676c1b750027 100644
--- a/security/openssh-portable/Makefile
+++ b/security/openssh-portable/Makefile
@@ -1,242 +1,244 @@
 PORTNAME=	openssh
 DISTVERSION=	9.9p1
-PORTREVISION=	0
+PORTREVISION=	1
 PORTEPOCH=	1
 CATEGORIES=	security
 MASTER_SITES=	OPENBSD/OpenSSH/portable
 PKGNAMESUFFIX?=	-portable
 
 MAINTAINER=	bdrewery@FreeBSD.org
 COMMENT=	The portable version of OpenBSD's OpenSSH
 WWW=		https://www.openssh.com/portable.html
 
 LICENSE=	OPENSSH
 LICENSE_NAME=	OpenSSH Licenses
 LICENSE_FILE=	${WRKSRC}/LICENCE
 LICENSE_PERMS=	dist-mirror dist-sell pkg-mirror pkg-sell auto-accept
 
 CONFLICTS?=		openssh-3.* ssh-1.* ssh2-3.* openssh-portable-devel
 
 USES=			alias autoreconf compiler:c11 cpe localbase ncurses \
 			pkgconfig ssl
 GNU_CONFIGURE=		yes
 GNU_CONFIGURE_MANPREFIX=	${PREFIX}/share
 CONFIGURE_ARGS=		--prefix=${PREFIX} \
 			--without-zlib-version-check \
 			--with-ssl-engine \
 			--with-mantype=man
 
 ETCOLD=			${PREFIX}/etc
 
 CPE_VENDOR=		openbsd
 
 FLAVORS=			default hpn gssapi
 default_CONFLICTS_INSTALL=	openssh-portable-hpn openssh-portable-gssapi \
 				openssh-portable-x509
 hpn_CONFLICTS_INSTALL=		openssh-portable openssh-portable-gssapi \
 				openssh-portable-x509
 hpn_PKGNAMESUFFIX=		-portable-hpn
 gssapi_CONFLICTS_INSTALL=	openssh-portable openssh-portable-hpn \
 				openssh-portable-x509
 gssapi_PKGNAMESUFFIX=		-portable-gssapi
 
 OPTIONS_DEFINE=		DOCS PAM TCP_WRAPPERS LIBEDIT BSM \
 			HPN KERB_GSSAPI \
 			LDNS NONECIPHER XMSS FIDO_U2F BLACKLISTD
 OPTIONS_DEFAULT=	LIBEDIT PAM TCP_WRAPPERS LDNS FIDO_U2F
 .if ${FLAVOR:U} == hpn
 OPTIONS_DEFAULT+=	HPN NONECIPHER
 .endif
 .if ${FLAVOR:U} == gssapi
 OPTIONS_DEFAULT+=	KERB_GSSAPI MIT
 .endif
 OPTIONS_RADIO=		KERBEROS
 OPTIONS_RADIO_KERBEROS=	MIT HEIMDAL HEIMDAL_BASE
 TCP_WRAPPERS_DESC=	tcp_wrappers support
 BSM_DESC=		OpenBSM Auditing
 KERB_GSSAPI_DESC=	Kerberos/GSSAPI patch (req: GSSAPI)
 HPN_DESC=		HPN-SSH patch
 LDNS_DESC=		SSHFP/LDNS support
 HEIMDAL_DESC=		Heimdal Kerberos (security/heimdal)
 HEIMDAL_BASE_DESC=	Heimdal Kerberos (base)
 MIT_DESC=		MIT Kerberos (security/krb5)
 NONECIPHER_DESC=	NONE Cipher support
 XMSS_DESC=		XMSS key support (experimental)
 FIDO_U2F_DESC=		FIDO/U2F support (security/libfido2)
 BLACKLISTD_DESC=	FreeBSD blacklistd(8) support
 
 OPTIONS_SUB=		yes
 
 PAM_EXTRA_PATCHES=	${FILESDIR}/extra-patch-pam-sshd_config
 
 TCP_WRAPPERS_EXTRA_PATCHES=${FILESDIR}/extra-patch-tcpwrappers
 
 LDNS_CONFIGURE_WITH=	ldns=${LOCALBASE}
 LDNS_LIB_DEPENDS=	libldns.so:dns/ldns
 LDNS_EXTRA_PATCHES=	${FILESDIR}/extra-patch-ldns
 
 HPN_CONFIGURE_WITH=		hpn
 NONECIPHER_CONFIGURE_WITH=	nonecipher
 
 MIT_LIB_DEPENDS=		libkrb5.so.3:security/krb5
 HEIMDAL_LIB_DEPENDS=		libkrb5.so.26:security/heimdal
 
 PAM_CONFIGURE_WITH=	pam
 TCP_WRAPPERS_CONFIGURE_WITH=	tcp-wrappers
 
 LIBEDIT_CONFIGURE_WITH=	libedit
 LIBEDIT_USES=		libedit
 BSM_CONFIGURE_ON=	--with-audit=bsm
 
 FIDO_U2F_LIB_DEPENDS=	libfido2.so:security/libfido2
 FIDO_U2F_CONFIGURE_ON=	--with-security-key-builtin
 FIDO_U2F_CONFIGURE_OFF=	--disable-security-key
 
 BLACKLISTD_EXTRA_PATCHES=	${FILESDIR}/extra-patch-blacklistd
 
 ETCDIR?=		${PREFIX}/etc/ssh
 
 .include <bsd.port.pre.mk>
 
 PATCH_SITES+=	http://mirror.shatow.net/freebsd/${PORTNAME}/:DEFAULT,hpn,gsskex
 
 # Must add this patch before HPN due to conflicts
 .if ${PORT_OPTIONS:MKERB_GSSAPI} || ${FLAVOR:U} == gssapi
 #BROKEN=	KERB_GSSAPI No patch for ${DISTVERSION} yet.
 .  if ${PORT_OPTIONS:MHPN} || ${PORT_OPTIONS:MNONECIPHER}
 # Needed glue for applying HPN patch without conflict
 EXTRA_PATCHES+=	${FILESDIR}/extra-patch-hpn-gss-glue
 .  endif
 # - See https://sources.debian.org/data/main/o/openssh/ for which subdir to
 # pull from.
 GSSAPI_DEBIAN_VERSION=	9.9p1
 GSSAPI_DEBIAN_SUBDIR=	${GSSAPI_DEBIAN_VERSION:U${DISTVERSION}}-1
 # - Debian does not use a versioned filename so we trick fetch to make one for
 # us with the ?<anything>=/ trick.
 PATCH_SITES+=	https://sources.debian.org/data/main/o/openssh/1:${GSSAPI_DEBIAN_SUBDIR}/debian/patches/gssapi.patch?dummy=/:gsskex
 # Bump this when updating the patch location
 GSSAPI_DISTVERSION=	9.9p1
 PATCHFILES+=	openssh-${GSSAPI_DISTVERSION:U${DISTVERSION}}-gsskex-all-debian-rh-${GSSAPI_DISTVERSION}.patch:-p1:gsskex
 EXTRA_PATCHES+=	${FILESDIR}/extra-patch-gssapi-kexgssc.c
 EXTRA_PATCHES+=	${FILESDIR}/extra-patch-gssapi-kexgsss.c
 .endif
 
 .if ${PORT_OPTIONS:MBLACKLISTD}
 CONFIGURE_LIBS+=	-lblacklist
 .endif
 
 # https://www.psc.edu/hpn-ssh https://github.com/rapier1/openssh-portable/tree/hpn-openssl1.1-7_7_P1
 .if ${PORT_OPTIONS:MHPN} || ${PORT_OPTIONS:MNONECIPHER}
 #BROKEN=			HPN: Not yet updated for ${DISTVERSION} yet.
 PORTDOCS+=		HPN-README
 HPN_VERSION=		14v15
 HPN_DISTVERSION=	7.7p1
 #PATCH_SITES+=		SOURCEFORGE/hpnssh/HPN-SSH%20${HPN_VERSION}%20${HPN_DISTVERSION}/:hpn
 #PATCHFILES+=		${PORTNAME}-${HPN_DISTVERSION}-hpnssh${HPN_VERSION}.diff.gz:-p1:hpn
 EXTRA_PATCHES+=		${FILESDIR}/extra-patch-hpn:-p2
 .elif !${PORT_OPTIONS:MHPN} && !${PORT_OPTIONS:MNONECIPHER}
 # Apply compatibility patch
 EXTRA_PATCHES+=		${FILESDIR}/extra-patch-hpn-compat
 .endif
 
 CONFIGURE_ARGS+=	--disable-utmp --disable-wtmp --disable-wtmpx --without-lastlog
 
 # Keep this last
 EXTRA_PATCHES+=		${FILESDIR}/extra-patch-version-addendum
 
 .if ${PORT_OPTIONS:MHEIMDAL_BASE} && ${PORT_OPTIONS:MKERB_GSSAPI}
 BROKEN=		KERB_GSSAPI Requires either MIT or HEMIDAL, does not build with base Heimdal currently
 .endif
 
 .if ${PORT_OPTIONS:MHEIMDAL_BASE} && !exists(/usr/lib/libkrb5.so)
 IGNORE=		you have selected HEIMDAL_BASE but do not have heimdal installed in base
 .endif
 
 .if ${PORT_OPTIONS:MMIT} || ${PORT_OPTIONS:MHEIMDAL} || ${PORT_OPTIONS:MHEIMDAL_BASE}
 .	if ${PORT_OPTIONS:MHEIMDAL_BASE}
 CONFIGURE_LIBS+=	-lgssapi_krb5
 CONFIGURE_ARGS+=	--with-kerberos5=/usr
 .	else
 CONFIGURE_LIBS+=	-lgssapi_krb5
 CONFIGURE_ARGS+=	--with-kerberos5=${LOCALBASE}
 .	endif
 .	if ${OPENSSLBASE} == "/usr"
 CONFIGURE_ARGS+=	--without-rpath
 LDFLAGS=		# empty
 .	endif
 .else
 .	if ${PORT_OPTIONS:MKERB_GSSAPI}
 IGNORE=	KERB_GSSAPI requires one of MIT HEIMDAL or HEIMDAL_BASE
 .	endif
 .endif
 
 .if ${OPENSSLBASE} != "/usr"
 CONFIGURE_ARGS+=	--with-ssl-dir=${OPENSSLBASE}
 .endif
 
 EMPTYDIR=		/var/empty
 
 USE_RC_SUBR=		openssh
 
 # After all
 CONFIGURE_ARGS+=	--sysconfdir=${ETCDIR} --with-privsep-path=${EMPTYDIR}
 .if !empty(CONFIGURE_LIBS)
 CONFIGURE_ARGS+=	--with-libs='${CONFIGURE_LIBS}'
 .endif
 
 CONFIGURE_ARGS+=	--with-xauth=${LOCALBASE}/bin/xauth
 
 RC_SCRIPT_NAME=		openssh
 VERSION_ADDENDUM_DEFAULT?=	${OPSYS}-${PKGNAME}
 
 CFLAGS+=	${CFLAGS_${CHOSEN_COMPILER_TYPE}}
 CFLAGS_gcc=	-Wno-stringop-truncation -Wno-stringop-overflow
 
 SSH_ASKPASS_PATH?=	${LOCALBASE}/bin/ssh-askpass
 
 post-patch:
 	@${REINPLACE_CMD} \
 	    -e 's|install: \(.*\) host-key check-config|install: \1|g' \
 	    ${WRKSRC}/Makefile.in
 	@${REINPLACE_CMD} \
 	    -e 's|$$[{(]libexecdir[})]/ssh-askpass|${SSH_ASKPASS_PATH}|' \
 	    ${WRKSRC}/Makefile.in ${WRKSRC}/configure.ac
 	@${REINPLACE_CMD} \
 	    -e 's|\(VersionAddendum\) none|\1 ${VERSION_ADDENDUM_DEFAULT}|' \
 	    ${WRKSRC}/sshd_config
 	@${REINPLACE_CMD} \
 	    -e 's|%%SSH_VERSION_FREEBSD_PORT%%|${VERSION_ADDENDUM_DEFAULT}|' \
 	    ${WRKSRC}/sshd_config.5
 	@${ECHO_CMD} '#define SSH_VERSION_FREEBSD_PORT	"${VERSION_ADDENDUM_DEFAULT}"' >> \
 		${WRKSRC}/version.h
 
 post-configure-XMSS-on:
 	@${ECHO_CMD} "#define WITH_XMSS 1" >> ${WRKSRC}/config.h
 
 post-configure-BLACKLISTD-on:
 	@${ECHO_CMD} "#define USE_BLACKLIST 1" >> ${WRKSRC}/config.h
 
 post-install:
 	${MV} ${STAGEDIR}${ETCDIR}/moduli \
 	    ${STAGEDIR}${ETCDIR}/moduli.sample
 	${MV} ${STAGEDIR}${ETCDIR}/ssh_config \
 	    ${STAGEDIR}${ETCDIR}/ssh_config.sample
 	${MV} ${STAGEDIR}${ETCDIR}/sshd_config \
 	    ${STAGEDIR}${ETCDIR}/sshd_config.sample
+	${MKDIR} ${STAGEDIR}${ETCDIR}/ssh_config.d \
+		 ${STAGEDIR}${ETCDIR}/sshd_config.d
 .if ${PORT_OPTIONS:MHPN} || ${PORT_OPTIONS:MNONECIPHER}
 	${MKDIR} ${STAGEDIR}${DOCSDIR}
 	${INSTALL_DATA} ${WRKSRC}/HPN-README ${STAGEDIR}${DOCSDIR}
 .endif
 
 test: build
 	cd ${WRKSRC} && ${SETENV} -i \
 		OBJ=${WRKDIR} ${MAKE_ENV:NHOME=*} \
 		TEST_SHELL=${SH} \
 		SUDO="${SUDO}" \
 		LOGNAME="${LOGNAME}" \
 		HOME="${HOME}" \
 		TEST_SSH_TRACE=yes \
 		PATH=${WRKSRC}:${PREFIX}/bin:${PREFIX}/sbin:${PATH} \
 		${MAKE_CMD} ${MAKE_FLAGS} ${MAKEFILE} ${MAKE_ARGS} tests
 
 .include <bsd.port.post.mk>
diff --git a/security/openssh-portable/files/patch-ssh_config b/security/openssh-portable/files/patch-ssh_config
new file mode 100644
index 000000000000..ea5fafad4d30
--- /dev/null
+++ b/security/openssh-portable/files/patch-ssh_config
@@ -0,0 +1,11 @@
+--- ssh_config.orig	2024-09-19 15:20:48.000000000 -0700
++++ ssh_config	2024-11-09 12:23:47.263548000 -0800
+@@ -17,6 +17,8 @@
+ # list of available options, their meanings and defaults, please see the
+ # ssh_config(5) man page.
+ 
++Include ssh_config.d/*.conf
++
+ # Host *
+ #   ForwardAgent no
+ #   ForwardX11 no
diff --git a/security/openssh-portable/files/patch-sshd_config b/security/openssh-portable/files/patch-sshd_config
index c19496486f4f..7b6bc14977c7 100644
--- a/security/openssh-portable/files/patch-sshd_config
+++ b/security/openssh-portable/files/patch-sshd_config
@@ -1,34 +1,33 @@
-!!!
-!!! Note files/extra-patch-pam-sshd_config contains more changes for default PAM option.
-!!!
---- sshd_config.orig	2022-02-11 18:49:55.062881000 +0000
-+++ sshd_config	2022-02-11 18:52:31.639435000 +0000
-@@ -10,6 +10,9 @@
+--- sshd_config.orig	2024-11-09 12:22:03.414050000 -0800
++++ sshd_config	2024-11-09 12:25:59.964286000 -0800
+@@ -10,6 +10,11 @@
  # possible, but leave them commented.  Uncommented options override the
  # default value.
  
 +# Note that some of FreeBSD's defaults differ from OpenBSD's, and
 +# FreeBSD has a few additional options.
++
++Include sshd_config.d/*.conf
 +
  #Port 22
  #AddressFamily any
  #ListenAddress 0.0.0.0
-@@ -37,8 +40,7 @@
+@@ -37,8 +42,7 @@
  #PubkeyAuthentication yes
  
  # The default is to check both .ssh/authorized_keys and .ssh/authorized_keys2
 -# but this is overridden so installations will only check .ssh/authorized_keys
 -AuthorizedKeysFile	.ssh/authorized_keys
 +#AuthorizedKeysFile .ssh/authorized_keys .ssh/authorized_keys2
  
  #AuthorizedPrincipalsFile none
  
-@@ -84,7 +86,7 @@
+@@ -84,7 +88,7 @@ AuthorizedKeysFile	.ssh/authorized_keys
  #AllowAgentForwarding yes
  #AllowTcpForwarding yes
  #GatewayPorts no
 -#X11Forwarding no
 +#X11Forwarding yes
  #X11DisplayOffset 10
  #X11UseLocalhost yes
  #PermitTTY yes
diff --git a/security/openssh-portable/files/patch-sshd_config.5 b/security/openssh-portable/files/patch-sshd_config.5
index 15d3ff7bf9d8..f5297c2a42c2 100644
--- a/security/openssh-portable/files/patch-sshd_config.5
+++ b/security/openssh-portable/files/patch-sshd_config.5
@@ -1,57 +1,59 @@
 --- sshd_config.5.orig	2022-02-11 18:50:00.822679000 +0000
 +++ sshd_config.5	2022-02-11 19:09:05.162504000 +0000
 @@ -701,7 +701,9 @@
  .Qq ssh -Q HostbasedAcceptedAlgorithms .
  This was formerly named HostbasedAcceptedKeyTypes.
  .It Cm HostbasedAuthentication
 -Specifies whether rhosts or /etc/hosts.equiv authentication together
 +Specifies whether rhosts or
 +.Pa /etc/hosts.equiv
 +authentication together
  with successful public key client host authentication is allowed
  (host-based authentication).
  The default is
-@@ -1416,6 +1434,13 @@
+@@ -1416,6 +1434,15 @@
  .Cm ethernet .
  The default is
  .Cm no .
 +Note that if
 +.Cm ChallengeResponseAuthentication
 +is
 +.Cm yes ,
 +the root user may be allowed in with its password even if
 +.Cm PermitRootLogin is set to
++.Cm prohibit-password
++or
 +.Cm without-password .
  .Pp
  Independent of this setting, the permissions of the selected
  .Xr tun 4
-@@ -1774,12 +1799,19 @@
+@@ -1774,12 +1801,19 @@
  .Xr sshd 8
  as a non-root user.
  The default is
 +.Cm yes ,
 +unless
 +.Nm sshd
 +was built without PAM support, in which case the default is
  .Cm no .
  .It Cm VersionAddendum
  Optionally specifies additional text to append to the SSH protocol banner
  sent by the server upon connection.
  The default is
 -.Cm none .
 +.Cm %%SSH_VERSION_FREEBSD_PORT%% .
 +The value
 +.Cm none
 +may be used to disable this.
  .It Cm X11DisplayOffset
  Specifies the first display number available for
  .Xr sshd 8 Ns 's
-@@ -1793,7 +1825,7 @@
+@@ -1793,7 +1827,7 @@
  or
  .Cm no .
  The default is
 -.Cm no .
 +.Cm yes .
  .Pp
  When X11 forwarding is enabled, there may be additional exposure to
  the server and to client displays if the
diff --git a/security/openssh-portable/pkg-plist b/security/openssh-portable/pkg-plist
index 276fd4a7590d..09c4267cc7ca 100644
--- a/security/openssh-portable/pkg-plist
+++ b/security/openssh-portable/pkg-plist
@@ -1,32 +1,34 @@
 bin/scp
 bin/sftp
 bin/ssh
 bin/ssh-add
 bin/ssh-agent
 bin/ssh-keygen
 bin/ssh-keyscan
 @sample %%ETCDIR%%/moduli.sample
 @sample %%ETCDIR%%/ssh_config.sample
 @sample %%ETCDIR%%/sshd_config.sample
+@dir %%ETCDIR%%/ssh_config.d
+@dir %%ETCDIR%%/sshd_config.d
 @postexec if [ -f %D/%%ETCDIR%%/ssh_host_ecdsa_key ] && grep -q DSA %D/%%ETCDIR%%/ssh_host_ecdsa_key; then echo; echo "\!/ Warning \!/"; echo; echo "Your %D/%%ETCDIR%%/ssh_host_ecdsa_key is not a valid ECDSA key. It is incorrectly"; echo "a DSA key due to a bug fixed in 2012 in the security/openssh-portable port."; echo; echo "Regenerate a proper one with: rm -f %D/%%ETCDIR%%/ssh_host_ecdsa_key*; service openssh restart"; echo; echo "Clients should not see any key change warning since the ECDSA was not valid and was not actually"; echo "used by the server."; echo; echo "\!/ Warning \!/"; fi
 sbin/sshd
 libexec/sftp-server
 libexec/ssh-keysign
 libexec/ssh-pkcs11-helper
 libexec/ssh-sk-helper
 libexec/sshd-session
 share/man/man1/sftp.1.gz
 share/man/man1/ssh-add.1.gz
 share/man/man1/ssh-agent.1.gz
 share/man/man1/ssh-keygen.1.gz
 share/man/man1/ssh-keyscan.1.gz
 share/man/man1/scp.1.gz
 share/man/man1/ssh.1.gz
 share/man/man5/moduli.5.gz
 share/man/man5/ssh_config.5.gz
 share/man/man5/sshd_config.5.gz
 share/man/man8/sftp-server.8.gz
 share/man/man8/ssh-keysign.8.gz
 share/man/man8/ssh-pkcs11-helper.8.gz
 share/man/man8/ssh-sk-helper.8.gz
 share/man/man8/sshd.8.gz