diff --git a/irc/weechat-otr/Makefile b/irc/weechat-otr/Makefile
index 453514195670..ed0936bb62b3 100644
--- a/irc/weechat-otr/Makefile
+++ b/irc/weechat-otr/Makefile
@@ -1,30 +1,33 @@
 PORTNAME=	weechat-otr
 DISTVERSIONPREFIX=	v
 DISTVERSION=	1.9.2
 CATEGORIES=	irc security python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	egypcio@FreeBSD.org
 COMMENT=	WeeChat script for Off-the-Record (OTR) messaging
 WWW=		https://github.com/mmb/weechat-otr
 
 LICENSE=	GPLv3
 
+DEPRECATED=	Depends on expired security/py-pycrypto (via security/py-potr)
+EXPIRATION_DATE=2022-12-31
+
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}potr>=1.0.1:security/py-potr@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}potr>=1.0.1:security/py-potr@${PY_FLAVOR} \
 		weechat:irc/weechat
 
 USES=		python
 USE_GITHUB=	yes
 GH_ACCOUNT=	mmb
 
 NO_BUILD=	yes
 
 PLIST_FILES=	${PYTHON_SITELIBDIR}/weechat/weechat_otr.py
 
 do-install:
 	${MKDIR} ${STAGEDIR}${PYTHON_SITELIBDIR}/weechat
 	${INSTALL_DATA} ${WRKSRC}/weechat_otr.py \
 		${STAGEDIR}${PYTHON_SITELIBDIR}/weechat/weechat_otr.py
 
 .include <bsd.port.mk>
diff --git a/sysutils/ansible4/Makefile b/sysutils/ansible4/Makefile
index 8f785e91c712..c45ecc6d27aa 100644
--- a/sysutils/ansible4/Makefile
+++ b/sysutils/ansible4/Makefile
@@ -1,52 +1,55 @@
 PORTNAME=	ansible
 DISTVERSION=	4.10.0
 CATEGORIES=	sysutils python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 PKGNAMESUFFIX=	4
 
 MAINTAINER=	0mp@FreeBSD.org
 COMMENT=	Radically simple IT automation
 WWW=		https://www.ansible.com/
 
 LICENSE=	GPLv3+
 LICENSE_FILE=	${WRKSRC}/COPYING
 
+DEPRECATED=	Depends on expired security/py-pycrypto (via sysutils/py-ansible-core211)
+EXPIRATION_DATE=2022-12-31
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}ansible-core211>0:sysutils/py-ansible-core211@${PY_FLAVOR}
 
 USES=		ansible:env cpe python:3.6+ shebangfix
 CPE_VENDOR=	redhat
 USE_PYTHON=	autoplist concurrent distutils
 
 SHEBANG_FILES=	ansible_collections/community/zabbix/roles/zabbix_proxy/files/install_semodule.bsx \
 		ansible_collections/community/zabbix/roles/zabbix_server/files/install_semodule.bsx \
 		ansible_collections/cyberark/conjur/ci/build_release \
 		ansible_collections/cyberark/conjur/ci/publish_to_galaxy \
 		ansible_collections/ovirt/ovirt/roles/disaster_recovery/files/ovirt-dr
 SHEBANG_GLOB=	*.py *.sh
 
 CONFLICTS_INSTALL=	${_ANSIBLE_PACKAGES:N${PKGBASE}}
 
 NO_ARCH=	yes
 
 DO_MAKE_TEST=	ansible -m ping
 TEST_TARGET=	localhost
 
 _ANSIBLE_VERSIONS=	1 2 23 24 25 26 27 28 4
 _ANSIBLE_PACKAGES=	${PYTHON_PKGNAMEPREFIX}ansible
 .for version in ${_ANSIBLE_VERSIONS}
 _ANSIBLE_PACKAGES+=	${PYTHON_PKGNAMEPREFIX}ansible${version}
 .endfor
 
 post-patch:
 	${FIND} ${WRKSRC} -type f -exec ${GREP} --null -El '(/etc/ansible|/usr/share/ansible)' {} + | ${XARGS} -n 500 -0 ${REINPLACE_CMD} \
 		-e 's|/etc/ansible|${ETCDIR}|g' \
 		-e 's|/usr/share/ansible|${DATADIR}|g'
 	${FIND} ${WRKSRC} -type f -name "*.bak" -delete
 
 .include <bsd.port.mk>
 
 # Make sure that we override the unique DATADIR and ETCDIR set
 # by the implicit USES=uniquefiles.
 DATADIR=	${ANSIBLE_DATADIR}
 ETCDIR=		${ANSIBLE_ETCDIR}