diff --git a/security/openssh-portable/Makefile b/security/openssh-portable/Makefile
index 97ba9e01adf9..69edba17e8cc 100644
--- a/security/openssh-portable/Makefile
+++ b/security/openssh-portable/Makefile
@@ -1,242 +1,242 @@
 PORTNAME=	openssh
-DISTVERSION=	9.8p1
-PORTREVISION=	1
+DISTVERSION=	9.9p1
+PORTREVISION=	0
 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=	9.8p1
-GSSAPI_DEBIAN_SUBDIR=	${GSSAPI_DEBIAN_VERSION:U${DISTVERSION}}-3
+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:${GSSAPI_DEBIAN_SUBDIR}/debian/patches/gssapi.patch?dummy=/:gsskex
 # Bump this when updating the patch location
-GSSAPI_DISTVERSION=	9.8p1
+GSSAPI_DISTVERSION=	9.9p1
 PATCHFILES+=	openssh-${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
 .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/distinfo b/security/openssh-portable/distinfo
index 11c1f02429d4..41138b4167db 100644
--- a/security/openssh-portable/distinfo
+++ b/security/openssh-portable/distinfo
@@ -1,5 +1,5 @@
-TIMESTAMP = 1722605239
-SHA256 (openssh-9.8p1.tar.gz) = dd8bd002a379b5d499dfb050dd1fa9af8029e80461f4bb6c523c49973f5a39f3
-SIZE (openssh-9.8p1.tar.gz) = 1910393
-SHA256 (openssh-9.8p1-gsskex-all-debian-rh-9.8p1.patch) = f5b93bf8076aa386afa63e98bb5b39b6e477b8ccb24d2d4b700f6cd685be6f78
-SIZE (openssh-9.8p1-gsskex-all-debian-rh-9.8p1.patch) = 125084
+TIMESTAMP = 1728410939
+SHA256 (openssh-9.9p1.tar.gz) = b343fbcdbff87f15b1986e6e15d6d4fc9a7d36066be6b7fb507087ba8f966c02
+SIZE (openssh-9.9p1.tar.gz) = 1964864
+SHA256 (openssh-9.9p1-gsskex-all-debian-rh-9.9p1.patch) = b8b590024137d54394fd46ebfe32f2b081d0744abdcdcacf6dd30d1c91339864
+SIZE (openssh-9.9p1-gsskex-all-debian-rh-9.9p1.patch) = 125233
diff --git a/security/openssh-portable/files/extra-patch-hpn-compat b/security/openssh-portable/files/extra-patch-hpn-compat
index 2460c27491fa..ab7617663feb 100644
--- a/security/openssh-portable/files/extra-patch-hpn-compat
+++ b/security/openssh-portable/files/extra-patch-hpn-compat
@@ -1,46 +1,46 @@
 ------------------------------------------------------------------------
 r294563 | des | 2016-01-22 05:13:46 -0800 (Fri, 22 Jan 2016) | 3 lines
 Changed paths:
    M /head/crypto/openssh/servconf.c
 
 Instead of removing the NoneEnabled option, mark it as unsupported.
 (should have done this in r291198, but didn't think of it until now)
 
 ------------------------------------------------------------------------
 ------------------------------------------------------------------------
 r294564 | des | 2016-01-22 06:22:11 -0800 (Fri, 22 Jan 2016) | 2 lines
 Changed paths:
    M /head/crypto/openssh/readconf.c
 
 r294563 was incomplete; re-add the client-side options as well.
 
 ------------------------------------------------------------------------
 
 --- readconf.c.orig	2023-12-19 17:09:41.366788000 -0800
 +++ readconf.c	2023-12-19 17:10:24.155247000 -0800
 @@ -329,6 +329,12 @@
  	{ "enableescapecommandline", oEnableEscapeCommandline },
  	{ "obscurekeystroketiming", oObscureKeystrokeTiming },
  	{ "channeltimeout", oChannelTimeout },
 +	{ "hpndisabled", oDeprecated },
 +	{ "hpnbuffersize", oDeprecated },
 +	{ "tcprcvbufpoll", oDeprecated },
 +	{ "tcprcvbuf", oDeprecated },
 +	{ "noneenabled", oUnsupported },
 +	{ "noneswitch", oUnsupported },
  
  	{ NULL, oBadOption }
  };
---- servconf.c.orig	2024-06-30 21:36:28.000000000 -0700
-+++ servconf.c	2024-07-01 13:29:27.091708000 -0700
-@@ -739,6 +739,10 @@ static struct {
- 	{ "channeltimeout", sChannelTimeout, SSHCFG_ALL },
+--- servconf.c.orig	2024-09-19 15:20:48.000000000 -0700
++++ servconf.c	2024-10-07 20:18:18.259726000 -0700
+@@ -746,6 +746,10 @@ static struct {
  	{ "unusedconnectiontimeout", sUnusedConnectionTimeout, SSHCFG_ALL },
  	{ "sshdsessionpath", sSshdSessionPath, SSHCFG_GLOBAL },
+ 	{ "refuseconnection", sRefuseConnection, SSHCFG_ALL },
 +	{ "noneenabled", sUnsupported, SSHCFG_ALL },
 +	{ "hpndisabled", sDeprecated, SSHCFG_ALL },
 +	{ "hpnbuffersize", sDeprecated, SSHCFG_ALL },
 +	{ "tcprcvbufpoll", sDeprecated, SSHCFG_ALL },
  	{ NULL, sBadOption, 0 }
  };
  
diff --git a/security/openssh-portable/files/patch-FreeBSD-logincap b/security/openssh-portable/files/patch-FreeBSD-logincap
deleted file mode 100644
index 78d772e8a024..000000000000
--- a/security/openssh-portable/files/patch-FreeBSD-logincap
+++ /dev/null
@@ -1,69 +0,0 @@
-(pulled from the PR)
-
-commit 27ceebbc2402e4c98203c7eef9696f4bd3d326f8
-Author: Ed Maste <emaste@FreeBSD.org>
-Date:   Tue Aug 31 15:30:50 2021 -0400
-
-    openssh: simplify login class restrictions
-
-    Login class-based restrictions were introduced in 5b400a39b8ad.  The
-    code was adapted for sshd's Capsicum sandbox and received many changes
-    over time, including at least fc3c19a9fcee, bd393de91cc3, and
-    e8c56fba2926.
-
-    During an attempt to upstream the work a much simpler approach was
-    suggested.  Adopt it now in the in-tree OpenSSH to reduce conflicts with
-    future updates.
-
-    Submitted by:   Yuchiro Naito (against OpenSSH-portable on GitHub)
-    Obtained from:  https://github.com/openssh/openssh-portable/pull/262
-    Reviewed by:    allanjude, kevans
-    MFC after:      2 weeks
-    Differential Revision:  https://reviews.freebsd.org/D31760
-
-
---- auth.c
-+++ auth.c
-@@ -566,6 +566,9 @@ getpwnamallow(struct ssh *ssh, const char *user)
- {
- #ifdef HAVE_LOGIN_CAP
- 	extern login_cap_t *lc;
-+#ifdef HAVE_AUTH_HOSTOK
-+	const char *from_host, *from_ip;
-+#endif
- #ifdef BSD_AUTH
- 	auth_session_t *as;
- #endif
-@@ -611,6 +614,21 @@ getpwnamallow(struct ssh *ssh, const char *user)
- 		debug("unable to get login class: %s", user);
- 		return (NULL);
- 	}
-+#ifdef HAVE_AUTH_HOSTOK
-+	from_host = auth_get_canonical_hostname(ssh, options.use_dns);
-+	from_ip = ssh_remote_ipaddr(ssh);
-+	if (!auth_hostok(lc, from_host, from_ip)) {
-+		debug("Denied connection for %.200s from %.200s [%.200s].",
-+		      pw->pw_name, from_host, from_ip);
-+		return (NULL);
-+	}
-+#endif /* HAVE_AUTH_HOSTOK */
-+#ifdef HAVE_AUTH_TIMEOK
-+	if (!auth_timeok(lc, time(NULL))) {
-+		debug("LOGIN %.200s REFUSED (TIME)", pw->pw_name);
-+		return (NULL);
-+	}
-+#endif /* HAVE_AUTH_TIMEOK */
- #ifdef BSD_AUTH
- 	if ((as = auth_open()) == NULL || auth_setpwd(as, pw) != 0 ||
- 	    auth_approval(as, lc, pw->pw_name, "ssh") <= 0) {
---- configure.ac
-+++ configure.ac
-@@ -1784,6 +1784,8 @@ AC_SUBST([PICFLAG])
- 
- dnl    Checks for library functions. Please keep in alphabetical order
- AC_CHECK_FUNCS([ \
-+	auth_hostok \
-+	auth_timeok \
- 	Blowfish_initstate \
- 	Blowfish_expandstate \
- 	Blowfish_expand0state \