diff --git a/security/py-pysaml2/Makefile b/security/py-pysaml2/Makefile
index cd0d6c16bcfb..f5f9afbb6dd3 100644
--- a/security/py-pysaml2/Makefile
+++ b/security/py-pysaml2/Makefile
@@ -1,49 +1,46 @@
 PORTNAME=	pysaml2
-PORTVERSION=	7.4.1
+PORTVERSION=	7.4.2
 CATEGORIES=	security devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Python implementation of SAML Version 2
 WWW=		https://github.com/IdentityPython/pysaml2
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cryptography>=3.1:security/py-cryptography@${PY_FLAVOR} \
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}poetry-core>=1.0.0:devel/py-poetry-core@${PY_FLAVOR}
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cryptography>=3.1,1:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}defusedxml>=0:devel/py-defusedxml@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}openssl>=0,1:security/py-openssl@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}dateutil>=0:devel/py-dateutil@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytz>=0,1:devel/py-pytz@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>=2<3:www/py-requests@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}xmlschema>=1.2.1:textproc/py-xmlschema@${PY_FLAVOR} \
 		xmlsec1:security/xmlsec1
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}mock>=0:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest>=0:devel/py-pytest@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}responses>=0:devel/py-responses@${PY_FLAVOR}
 
-USES=		cpe python
-USE_PYTHON=	autoplist concurrent distutils
+USES=		cpe python:3.9+ shebangfix
+USE_PYTHON=	autoplist concurrent pep517
 
 NO_ARCH=	yes
 
 CPE_VENDOR=	pysaml2_project
 
+SHEBANG_FILES=	src/saml2/authn_context/timesync.py
+
 OPTIONS_DEFINE=	S2REPOZE
 S2REPOZE_DESC=	Repoze module support
 
 S2REPOZE_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}Paste>=0:www/py-paste@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}repoze.who>=0:devel/py-repoze.who@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}zope.interface>=0:devel/py-zope.interface@${PY_FLAVOR}
 
-.include <bsd.port.pre.mk>
-
-.if ${PYTHON_REL} < 30900
-RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}importlib-resources>=0:devel/py-importlib-resources@${PY_FLAVOR}
-.endif
-
 do-test:
 	cd ${WRKSRC} && ${PYTHON_CMD} -m pytest -rs -v
 
-.include <bsd.port.post.mk>
+.include <bsd.port.mk>
diff --git a/security/py-pysaml2/distinfo b/security/py-pysaml2/distinfo
index f81047dd8664..8810c5e699a0 100644
--- a/security/py-pysaml2/distinfo
+++ b/security/py-pysaml2/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1677771355
-SHA256 (pysaml2-7.4.1.tar.gz) = 28a0a513d3fb219947314101b9a302f4c7df60f90677d82a64077edd2db58943
-SIZE (pysaml2-7.4.1.tar.gz) = 342196
+TIMESTAMP = 1688166320
+SHA256 (pysaml2-7.4.2.tar.gz) = 2bc5147b3b2f902a9131bf08240c068becea29994aafb7654a63d7270ac5b63b
+SIZE (pysaml2-7.4.2.tar.gz) = 341425