diff --git a/security/py-asyncssh/Makefile b/security/py-asyncssh/Makefile
index ff1f2de3df73..52e51845c760 100644
--- a/security/py-asyncssh/Makefile
+++ b/security/py-asyncssh/Makefile
@@ -1,41 +1,41 @@
 PORTNAME=	asyncssh
-PORTVERSION=	2.13.2
+PORTVERSION=	2.14.0
 CATEGORIES=	security python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Asynchronous SSHv2 client and server library
 WWW=		https://github.com/ronf/asyncssh
 
 LICENSE=	EPL
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}typing-extensions>=3.6:devel/py-typing-extensions@${PY_FLAVOR}
 
 USES=		cpe python
 USE_PYTHON=	autoplist concurrent cryptography distutils unittest
 
 NO_ARCH=	yes
 
 CPE_VENDOR=	asyncssh_project
 
 OPTIONS_DEFINE=	BCRYPT FIDO2 GSSAPI LIBNACL NETTLE PKCS11 PYOPENSSL
 OPTIONS_DEFAULT=BCRYPT FIDO2 PYOPENSSL
 BCRYPT_DESC=	OpenSSH private key encryption
 FIDO2_DESC=	FIDO2 support
 GSSAPI_DESC=	GSSAPI key exchange and authentication
 LIBNACL_DESC=	Curve25519, Ed25519 and Chacha20-Poly1305 support
 NETTLE_DESC=	UMAC cryptographic hashes
 PKCS11_DESC=	PKCS \#11 support
 PYOPENSSL_DESC=	X.509 certificate authentication
 
 BCRYPT_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}bcrypt>=3.1.3:security/py-bcrypt@${PY_FLAVOR}
 FIDO2_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}fido2>=0.9.2:security/py-fido2@${PY_FLAVOR}
 GSSAPI_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}gssapi>=1.2.0:security/py-gssapi@${PY_FLAVOR}
 LIBNACL_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}libnacl>=1.4.2:security/py-libnacl@${PY_FLAVOR}
 NETTLE_LIB_DEPENDS=	libnettle.so:security/nettle
 PKCS11_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}python-pkcs11>=0.7.0:security/py-python-pkcs11@${PY_FLAVOR}
-PYOPENSSL_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}openssl>=17.0.0:security/py-openssl@${PY_FLAVOR}
+PYOPENSSL_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}openssl>=23.0.0,1:security/py-openssl@${PY_FLAVOR}
 
 .include <bsd.port.mk>
diff --git a/security/py-asyncssh/distinfo b/security/py-asyncssh/distinfo
index ec86fff2259a..ffe9d37477c9 100644
--- a/security/py-asyncssh/distinfo
+++ b/security/py-asyncssh/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1688166310
-SHA256 (asyncssh-2.13.2.tar.gz) = 991e531c4bb7dbec62b754878d96a3246338aac11a28ce3c3e99018fb2f5828c
-SIZE (asyncssh-2.13.2.tar.gz) = 498674
+TIMESTAMP = 1696432960
+SHA256 (asyncssh-2.14.0.tar.gz) = e03ef2d131fbb4371b4018718452ce8c735a48edfe0139d2abdce4c187a459c3
+SIZE (asyncssh-2.14.0.tar.gz) = 501088