diff --git a/devel/py-rauth/Makefile b/devel/py-rauth/Makefile
index c5710d0a7341..f63e683a2ae1 100644
--- a/devel/py-rauth/Makefile
+++ b/devel/py-rauth/Makefile
@@ -1,30 +1,33 @@
 # Created by: Kubilay Kocak <koobs@FreeBSD.org>
 
 PORTNAME=	rauth
 PORTVERSION=	0.7.2
 CATEGORIES=	devel www python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	bofh@FreeBSD.org
 COMMENT=	Python library for OAuth 1.0/a, 2.0, and Ofly consumers
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}requests>=1.2.3:www/py-requests@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}nose>=1.2.1:devel/py-nose@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mock>=1.0.1:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>=2.5:security/py-pycrypto@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_GITHUB=	yes
 USE_PYTHON=	distutils autoplist
 
 GH_ACCOUNT=	litl
 
 NO_ARCH=	yes
 
 do-test:
 	@cd ${WRKSRC} && ${PYTHON_CMD} ${PYDISTUTILS_SETUP} test
 
 .include <bsd.port.mk>
diff --git a/net/py-impacket/Makefile b/net/py-impacket/Makefile
index fe038ad6f418..b6031214c75d 100644
--- a/net/py-impacket/Makefile
+++ b/net/py-impacket/Makefile
@@ -1,34 +1,37 @@
 # Created by: Marcin Jessa <yazzy@yazzy.org>
 
 PORTNAME=	impacket
 PORTVERSION=	0.9.17
 CATEGORIES=	net python
 MASTER_SITES=	CHEESESHOP \
 		https://github.com/CoreSecurity/impacket/releases/download/impacket_${PORTVERSION:S,.,_,g}/
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	contato@kanazuchi.com
 COMMENT=	Collection of Python classes providing access to network packets
 
 LICENSE=	APACHE11 ZLIB
 LICENSE_COMB=	multi
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pyasn1>=0:devel/py-pyasn1@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pcapy>=0:net/py-pcapy@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>=0:security/py-pycrypto@${PY_FLAVOR}
 
 USES=		dos2unix python:3.6+
 USE_PYTHON=	autoplist distutils
 NO_ARCH=	yes
 
 PORTDOCS=	*
 
 OPTIONS_DEFINE=	DOCS
 
 post-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	${INSTALL_DATA} ${WRKSRC}/README.md ${STAGEDIR}${DOCSDIR}
 	cd ${WRKSRC} && ${COPYTREE_SHARE} tests ${STAGEDIR}${DOCSDIR}
 
 .include <bsd.port.mk>
diff --git a/net/scapy/Makefile b/net/scapy/Makefile
index cfa02f82f723..3772f4bd8fba 100644
--- a/net/scapy/Makefile
+++ b/net/scapy/Makefile
@@ -1,56 +1,59 @@
 # Created by: vanhu <vanhu@netasq.com>
 
 PORTNAME=	scapy
 PORTVERSION=	2.4.5
 CATEGORIES=	net python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	bofh@FreeBSD.org
 COMMENT=	Powerful interactive packet manipulation program in python
 
 LICENSE=	GPLv2
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}libdnet>0:net/py-libdnet@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pypcap>0:net/py-pypcap@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}cryptography>0:security/py-cryptography@${PY_FLAVOR}
 
 USES=		cpe python:3.7+
 USE_PYTHON=	autoplist concurrent distutils
 
 NO_ARCH=	yes
 
 OPTIONS_DEFINE=	GRAPH IPYTHON P0F_BASE MANUF MATPLOT NMAP PYCRYPTO PYX SOX
 GRAPH_DESC=	graph generation and visualization
 IPYTHON_DESC=	Use IPython (enhanced interactive shell)
 MANUF_DESC=	wireshark's MANUF MAC database
 MATPLOT_DESC=	Install python matplotlibs
 NMAP_DESC=	nmap OS signatures database
 P0F_BASE_DESC=	p0f OS signatures database
 PYCRYPTO_DESC=	Use py-crypto for WEP decoding
 PYX_DESC=	PostScript and PDF graphs drawing
 SOX_DESC=	Support for VoIP
 
 GRAPH_USES=		magick:6,run
 GRAPH_RUN_DEPENDS=	${LOCALBASE}/bin/dot:graphics/graphviz
 IPYTHON_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}ipython>0:devel/ipython@${PY_FLAVOR}
 NMAP_RUN_DEPENDS=	${LOCALBASE}/share/nmap/nmap-os-db:security/nmap
 MANUF_RUN_DEPENDS=	${LOCALBASE}/share/wireshark/manuf:net/wireshark
 MATPLOT_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}matplotlib>0:math/py-matplotlib@${PY_FLAVOR}
 P0F_BASE_RUN_DEPENDS=	${LOCALBASE}/etc/p0f.fp:net-mgmt/p0f
 PYCRYPTO_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pycrypto>0:security/py-pycrypto@${PY_FLAVOR}
 PYX_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pyx>0:graphics/py-pyx@${PY_FLAVOR}
 SOX_RUN_DEPENDS=	${LOCALBASE}/bin/sox:audio/sox
 
 post-patch:
 	@${REINPLACE_CMD} "s,share/man/man1,man/man1," ${WRKSRC}/setup.py
 	@${REINPLACE_CMD} "s,pdflatex,pdftex," ${WRKSRC}/scapy/extlib.py
 	@${REINPLACE_CMD} "s,/usr/share/,${LOCALBASE}/share/," \
 		${WRKSRC}/scapy/modules/nmap.py
 	@${REINPLACE_CMD} "s,/etc/,${LOCALBASE}/etc/," \
 		${WRKSRC}/scapy/modules/p0f.py
 	@${REINPLACE_CMD} 's|"use" in line|"use" in line or "nhop" in line|' \
 		${WRKSRC}/scapy/arch/unix.py
 
 .include <bsd.port.mk>
diff --git a/security/pwman3/Makefile b/security/pwman3/Makefile
index c9d271f2fb97..cfdeb82a3fdd 100644
--- a/security/pwman3/Makefile
+++ b/security/pwman3/Makefile
@@ -1,22 +1,25 @@
 # Created by: Yarodin <yarodin@gmail.com>
 
 PORTNAME=	pwman3
 PORTVERSION=	0.0.6
 PORTREVISION=	2
 CATEGORIES=	security python
 MASTER_SITES=	http://pwman.bleurgh.com/~ivan/pwman3/source/ \
 		http://source.antisupport.com/pwman3/
 DISTNAME=	Pwman3-${PORTVERSION}
 
 MAINTAINER=	yarodin@gmail.com
 COMMENT=	Console password management application with sql storage
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pycrypto>=2.0:security/py-pycrypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sqlite3>=0:databases/py-sqlite3@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	distutils autoplist concurrent optsuffix
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/security/py-YubiOTP/Makefile b/security/py-YubiOTP/Makefile
index 2dcb3f649bcc..4318eb0486bf 100644
--- a/security/py-YubiOTP/Makefile
+++ b/security/py-YubiOTP/Makefile
@@ -1,20 +1,23 @@
 # Created by: Carlo Strub <cs@FreeBSD.org>
 
 PORTNAME=	YubiOTP
 PORTVERSION=	1.0.0
 CATEGORIES=	security python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	cs@FreeBSD.org
 COMMENT=	Library for verifying YubiKey OTP tokens
 
 LICENSE=	BSD2CLAUSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}six>0:devel/py-six@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>0:security/py-pycrypto@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	autoplist distutils
 
 .include <bsd.port.mk>
diff --git a/security/py-keyrings.alt/Makefile b/security/py-keyrings.alt/Makefile
index 819a45f09c55..5e4fd7ec1ddf 100644
--- a/security/py-keyrings.alt/Makefile
+++ b/security/py-keyrings.alt/Makefile
@@ -1,37 +1,40 @@
 # Created by: Douglas Thrift <douglas@douglasthrift.net>
 
 PORTNAME=	keyrings.alt
 PORTVERSION=	3.1.1
 CATEGORIES=	security python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	douglas@douglasthrift.net
 COMMENT=	Alternate Python keyring implementations
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools_scm>=1.15.0:devel/py-setuptools_scm@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}six>0:devel/py-six@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}keyring>=10.3.1:security/py-keyring@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>0:security/py-pycrypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}fs>=0.5:devel/py-fs@${PY_FLAVOR}
 
 USES=		python:3.6+ pytest
 USE_PYTHON=	autoplist distutils
 
 NO_ARCH=	yes
 
 OPTIONS_DEFINE=		ENCRYPTED_FILE GNOME_KEYRING PYFS
 ENCRYPTED_FILE_DESC=	Install pycrypto to support the Encrypted File backend
 GNOME_KEYRING_DESC=	Install GNOME Keyring to support the Gnome backend
 PYFS_DESC=		Install pyfilesystem to support the pyfs backend
 
 ENCRYPTED_FILE_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pycrypto>=2.5:security/py-pycrypto@${PY_FLAVOR}
 GNOME_KEYRING_USES=		gnome
 GNOME_KEYRING_USE=		GNOME=pygobject3
 PYFS_RUN_DEPENDS=		${PYTHON_PKGNAMEPREFIX}fs>=0.5:devel/py-fs@${PY_FLAVOR}
 
 .include <bsd.port.mk>
diff --git a/security/py-potr/Makefile b/security/py-potr/Makefile
index e8f0f0c9aaca..05ad74c349b3 100644
--- a/security/py-potr/Makefile
+++ b/security/py-potr/Makefile
@@ -1,19 +1,22 @@
 PORTNAME=	potr
 PORTVERSION=	1.0.1
 CATEGORIES=	security python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	python-${PORTNAME}-${PORTVERSION}
 
 MAINTAINER=	rm@FreeBSD.org
 COMMENT=	Pure Python Off-The-Record encryption
 
 LICENSE=	LGPL3
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pycrypto>0:security/py-pycrypto@${PY_FLAVOR}
 
 USES=		python:3.6+ zip
 USE_PYTHON=	autoplist distutils
 
 .include <bsd.port.mk>
diff --git a/security/py-stem/Makefile b/security/py-stem/Makefile
index 9e390522ce75..d858aaac2b44 100644
--- a/security/py-stem/Makefile
+++ b/security/py-stem/Makefile
@@ -1,27 +1,30 @@
 # Created by: Carlo Strub
 
 PORTNAME=	stem
 PORTVERSION=	1.8.0
 CATEGORIES=	security net python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	cs@FreeBSD.org
 COMMENT=	Python controller library for Tor
 
 LICENSE=	LGPL3
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pycrypto>0:security/py-pycrypto@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyflakes>0:devel/py-pyflakes@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycodestyle>0:devel/py-pycodestyle@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	distutils autoplist concurrent
 NO_ARCH=	yes
 
 do-test:
 	@cd ${WRKSRC} && ${PYTHON_CMD} run_tests.py -a
 
 .include <bsd.port.mk>
diff --git a/security/py-yubikey-manager/Makefile b/security/py-yubikey-manager/Makefile
index af756323aab3..8020c896d474 100644
--- a/security/py-yubikey-manager/Makefile
+++ b/security/py-yubikey-manager/Makefile
@@ -1,35 +1,38 @@
 PORTNAME=	yubikey-manager
 PORTVERSION=	4.0.9
 PORTREVISION=	1
 CATEGORIES=	security python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	egypcio@FreeBSD.org
 COMMENT=	Python library and command line tool for configuring a YubiKey
 
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/COPYING
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 BUILD_DEPENDS=	${RUN_DEPENDS}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}click>0:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}fido2>0:security/py-fido2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}openssl>0:security/py-openssl@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyscard>0:security/py-pyscard@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>0:security/py-pycrypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyusb>0:devel/py-pyusb@${PY_FLAVOR} \
 		RSA_SecurID_getpasswd:devel/libccid \
 		pcsc-spy:devel/pcsc-lite \
 		u2f-host:security/libu2f-host \
 		ykpersonalize:security/ykpers
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}makefun>0:devel/py-makefun@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR}
 
 USES=		dos2unix python:3.6+
 USE_PYTHON=	autoplist concurrent distutils unittest
 
 DOS2UNIX_GLOB=	*.adoc *.py
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/sysutils/py-ansible-base/Makefile b/sysutils/py-ansible-base/Makefile
index b4732d88c5c1..238669c75ef7 100644
--- a/sysutils/py-ansible-base/Makefile
+++ b/sysutils/py-ansible-base/Makefile
@@ -1,106 +1,109 @@
 PORTNAME=	ansible-base
 DISTVERSION=	2.10.17
 CATEGORIES=	sysutils python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 PATCH_SITES=	https://github.com/ansible/ansible/commit/
 PATCHFILES=	6459fbb7bcf792aac9208d7851bf1edeb0495295.patch:-p1
 
 MAINTAINER=	0mp@FreeBSD.org
 COMMENT=	Radically simple IT automation
 
 LICENSE=	GPLv3+
 LICENSE_FILE=	${WRKSRC}/COPYING
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cryptography>0:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}Jinja2>0:devel/py-Jinja2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=0:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}resolvelib05>0:devel/py-resolvelib05@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}yaml>0:devel/py-yaml@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}bcrypt>=0:security/py-bcrypt@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}boto3>0:www/py-boto3@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}nose>0:devel/py-nose@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}passlib>0:security/py-passlib@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>=0:security/py-pycrypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-mock>0:devel/py-pytest-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-xdist>0:devel/py-pytest-xdist@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>0:www/py-requests@${PY_FLAVOR}
 
 USES=		ansible:env cpe gmake python:3.6+ shebangfix
 CPE_VENDOR=	redhat
 CPE_PRODUCT=	ansible
 USE_PYTHON=	autoplist concurrent distutils
 
 SHEBANG_REGEX=	[.]/test/.*[.]py
 
 TEST_ARGS=	VERSION=${DISTVERSION} \
 		PYTHON=${PYTHON_CMD} \
 		DATE=
 TEST_ENV=	PYTHON_VERSION=${PYTHON_VER} \
 		TEST_FLAGS=-vv
 TEST_TARGET=	tests
 
 CONFLICTS=	py*-ansible-core py*-ansible2
 
 NO_ARCH=	yes
 
 PLIST_FILES=	share/man/man1/ansible-config.1.gz \
 		share/man/man1/ansible-console.1.gz \
 		share/man/man1/ansible-doc.1.gz \
 		share/man/man1/ansible-galaxy.1.gz \
 		share/man/man1/ansible-inventory.1.gz \
 		share/man/man1/ansible-playbook.1.gz \
 		share/man/man1/ansible-pull.1.gz \
 		share/man/man1/ansible-vault.1.gz \
 		share/man/man1/ansible.1.gz
 PORTEXAMPLES=	ansible.cfg hosts
 
 OPTIONS_DEFINE=	DOCS EXAMPLES
 
 post-patch:
 # Preserve the original paths in
 # test/units/cli/galaxy/test_execute_list_collection.py.
 # Replacing /usr/share/ansible breaks tests.
 	${FIND} ${WRKSRC} -not -regex '${WRKSRC}/test/units/cli/galaxy/test_execute_list_collection.py' -type f -print0 | \
 		${XARGS} -0 ${REINPLACE_CMD} \
 			-e 's|/etc/ansible|${ETCDIR}|g' \
 			-e 's|/usr/share/ansible|${DATADIR}|g'
 	${FIND} ${WRKSRC} -type f -name "*.bak" -delete
 
 post-install:
 	@${MKDIR} ${STAGEDIR}${MAN1PREFIX}/man/man1
 	${INSTALL_MAN} ${WRKSRC}/docs/man/man1/*.1 \
 		${STAGEDIR}${MAN1PREFIX}/share/man/man1
 
 post-install-EXAMPLES-on:
 	@${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
 	${INSTALL_DATA} ${WRKSRC}/examples/ansible.cfg ${STAGEDIR}${EXAMPLESDIR}
 	${INSTALL_DATA} ${WRKSRC}/examples/hosts ${STAGEDIR}${EXAMPLESDIR}
 
 post-stage:
 	${FIND} ${STAGEDIR}${PREFIX}/bin -type l -name ansible-\* -lname ansible \
 		-execdir ${RLN} ansible-${PYTHON_VER} {} \;
 # USE_PYTHON=autoplist doesn't add this file to pkg-plist.
 	${RM} ${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}/ansible_test/_data/injector/ansible-inventory
 
 pre-test:
 # This one file does not get its paths replaced correctly in post-patch.
 	${REINPLACE_CMD} 's|"/etc"|"${ETCDIR:H}"|g' \
 		${WRKSRC}/test/units/playbook/test_helpers.py
 # This test constructs a Python script inline and uses an invalid path to it.
 	${REINPLACE_CMD} 's|/usr/bin/python|${PYTHON_CMD}|' \
 		${WRKSRC}/test/units/modules/test_async_wrapper.py
 # Disable some tests:
 # - Skip the SELinux tests, it's not present on FreeBSD.
 	${RM} ${WRKSRC}/test/units/module_utils/basic/test_selinux.py
 # - Failure detecting that emojis are of width 2 instead of 1.
 	${RM} ${WRKSRC}/test/units/utils/test_display.py
 
 .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}
diff --git a/sysutils/py-ansible-core/Makefile b/sysutils/py-ansible-core/Makefile
index 58ccf1e7ece3..d6189f7e4008 100644
--- a/sysutils/py-ansible-core/Makefile
+++ b/sysutils/py-ansible-core/Makefile
@@ -1,102 +1,105 @@
 PORTNAME=	ansible-core
 DISTVERSION=	2.12.4
 CATEGORIES=	sysutils python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	0mp@FreeBSD.org
 COMMENT=	Radically simple IT automation
 
 LICENSE=	GPLv3+
 LICENSE_FILE=	${WRKSRC}/COPYING
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cryptography>0:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}Jinja2>0:devel/py-Jinja2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=0:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}resolvelib05>=0.5.3<0.6:devel/py-resolvelib05@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}yaml>0:devel/py-yaml@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}bcrypt>=0:security/py-bcrypt@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}boto3>0:www/py-boto3@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}nose>0:devel/py-nose@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}passlib>0:security/py-passlib@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>=0:security/py-pycrypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-mock>0:devel/py-pytest-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-xdist>0:devel/py-pytest-xdist@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>0:www/py-requests@${PY_FLAVOR}
 
 USES=		ansible:env cpe gmake python:3.8+ shebangfix
 CPE_VENDOR=	redhat
 CPE_PRODUCT=	ansible
 USE_PYTHON=	autoplist concurrent distutils
 
 SHEBANG_REGEX=	[.]/test/.*[.]py
 
 TEST_ARGS=	VERSION=${DISTVERSION} \
 		PYTHON=${PYTHON_CMD} \
 		DATE=
 TEST_ENV=	PYTHON_VERSION=${PYTHON_VER}
 TEST_TARGET=	tests
 
 CONFLICTS=	py*-ansible-base py*-ansible2 py-ansible-core211
 
 NO_ARCH=	yes
 
 PLIST_FILES=	share/man/man1/ansible-config.1.gz \
 		share/man/man1/ansible-console.1.gz \
 		share/man/man1/ansible-doc.1.gz \
 		share/man/man1/ansible-galaxy.1.gz \
 		share/man/man1/ansible-inventory.1.gz \
 		share/man/man1/ansible-playbook.1.gz \
 		share/man/man1/ansible-pull.1.gz \
 		share/man/man1/ansible-vault.1.gz \
 		share/man/man1/ansible.1.gz
 PORTEXAMPLES=	ansible.cfg hosts
 
 OPTIONS_DEFINE=	DOCS EXAMPLES
 
 post-patch:
 # Preserve the original paths in
 # test/units/cli/galaxy/test_execute_list_collection.py.
 # Replacing /usr/share/ansible breaks tests.
 	${FIND} ${WRKSRC} -not -regex '${WRKSRC}/test/units/cli/galaxy/test_execute_list_collection.py' -type f -print0 | \
 		${XARGS} -0 ${REINPLACE_CMD} \
 			-e 's|/etc/ansible|${ETCDIR}|g' \
 			-e 's|/usr/share/ansible|${DATADIR}|g'
 	${FIND} ${WRKSRC} -type f -name "*.bak" -delete
 
 post-install:
 	@${MKDIR} ${STAGEDIR}${MAN1PREFIX}/man/man1
 	${INSTALL_MAN} ${WRKSRC}/docs/man/man1/*.1 \
 		${STAGEDIR}${MAN1PREFIX}/share/man/man1
 
 post-install-EXAMPLES-on:
 	@${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
 	${INSTALL_DATA} ${WRKSRC}/examples/ansible.cfg ${STAGEDIR}${EXAMPLESDIR}
 	${INSTALL_DATA} ${WRKSRC}/examples/hosts ${STAGEDIR}${EXAMPLESDIR}
 
 post-stage:
 	${FIND} ${STAGEDIR}${PREFIX}/bin -type l -name ansible-\* -lname ansible \
 		-execdir ${RLN} ansible-${PYTHON_VER} {} \;
 # USE_PYTHON=autoplist doesn't add this file to pkg-plist.
 	${RM} ${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}/ansible_test/_data/injector/ansible-inventory
 
 pre-test:
 # This one file does not get its paths replaced correctly in post-patch.
 	${REINPLACE_CMD} 's|"/etc"|"${ETCDIR:H}"|g' \
 		${WRKSRC}/test/units/playbook/test_helpers.py
 # This test constructs a Python script inline and uses an invalid path to it.
 	${REINPLACE_CMD} 's|/usr/bin/python|${PYTHON_CMD}|' \
 		${WRKSRC}/test/units/modules/test_async_wrapper.py
 # Skip the SELinux tests, it's not present on FreeBSD.
 	${RM} ${WRKSRC}/test/units/module_utils/basic/test_selinux.py
 # Disable some failing tests. They fail to detect that emoji are of width 2 istead of 1.
 	${RM} ${WRKSRC}/test/units/utils/test_display.py
 
 .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}
diff --git a/sysutils/py-ansible-core211/Makefile b/sysutils/py-ansible-core211/Makefile
index 6d65cdd6a5ac..eb998d17ff93 100644
--- a/sysutils/py-ansible-core211/Makefile
+++ b/sysutils/py-ansible-core211/Makefile
@@ -1,103 +1,106 @@
 PORTNAME=	ansible-core
 DISTVERSION=	2.11.10
 CATEGORIES=	sysutils python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 PKGNAMESUFFIX=	211
 
 MAINTAINER=	0mp@FreeBSD.org
 COMMENT=	Radically simple IT automation
 
 LICENSE=	GPLv3+
 LICENSE_FILE=	${WRKSRC}/COPYING
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cryptography>0:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}Jinja2>0:devel/py-Jinja2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=0:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}resolvelib05>=0.5.3<0.6:devel/py-resolvelib05@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}yaml>0:devel/py-yaml@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}bcrypt>=0:security/py-bcrypt@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}boto3>0:www/py-boto3@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}nose>0:devel/py-nose@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}passlib>0:security/py-passlib@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>=0:security/py-pycrypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-mock>0:devel/py-pytest-mock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-xdist>0:devel/py-pytest-xdist@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>0:www/py-requests@${PY_FLAVOR}
 
 USES=		ansible:env cpe gmake python:3.6+ shebangfix
 CPE_VENDOR=	redhat
 CPE_PRODUCT=	ansible
 USE_PYTHON=	autoplist concurrent distutils
 
 SHEBANG_REGEX=	[.]/test/.*[.]py
 
 TEST_ARGS=	VERSION=${DISTVERSION} \
 		PYTHON=${PYTHON_CMD} \
 		DATE=
 TEST_ENV=	PYTHON_VERSION=${PYTHON_VER}
 TEST_TARGET=	tests
 
 CONFLICTS=	py*-ansible-base py*-ansible-core py*-ansible2
 
 NO_ARCH=	yes
 
 PLIST_FILES=	share/man/man1/ansible-config.1.gz \
 		share/man/man1/ansible-console.1.gz \
 		share/man/man1/ansible-doc.1.gz \
 		share/man/man1/ansible-galaxy.1.gz \
 		share/man/man1/ansible-inventory.1.gz \
 		share/man/man1/ansible-playbook.1.gz \
 		share/man/man1/ansible-pull.1.gz \
 		share/man/man1/ansible-vault.1.gz \
 		share/man/man1/ansible.1.gz
 PORTEXAMPLES=	ansible.cfg hosts
 
 OPTIONS_DEFINE=	DOCS EXAMPLES
 
 post-patch:
 # Preserve the original paths in
 # test/units/cli/galaxy/test_execute_list_collection.py.
 # Replacing /usr/share/ansible breaks tests.
 	${FIND} ${WRKSRC} -not -regex '${WRKSRC}/test/units/cli/galaxy/test_execute_list_collection.py' -type f -print0 | \
 		${XARGS} -0 ${REINPLACE_CMD} \
 			-e 's|/etc/ansible|${ETCDIR}|g' \
 			-e 's|/usr/share/ansible|${DATADIR}|g'
 	${FIND} ${WRKSRC} -type f -name "*.bak" -delete
 
 post-install:
 	@${MKDIR} ${STAGEDIR}${MAN1PREFIX}/man/man1
 	${INSTALL_MAN} ${WRKSRC}/docs/man/man1/*.1 \
 		${STAGEDIR}${MAN1PREFIX}/share/man/man1
 
 post-install-EXAMPLES-on:
 	@${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
 	${INSTALL_DATA} ${WRKSRC}/examples/ansible.cfg ${STAGEDIR}${EXAMPLESDIR}
 	${INSTALL_DATA} ${WRKSRC}/examples/hosts ${STAGEDIR}${EXAMPLESDIR}
 
 post-stage:
 	${FIND} ${STAGEDIR}${PREFIX}/bin -type l -name ansible-\* -lname ansible \
 		-execdir ${RLN} ansible-${PYTHON_VER} {} \;
 # USE_PYTHON=autoplist doesn't add this file to pkg-plist.
 	${RM} ${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}/ansible_test/_data/injector/ansible-inventory
 
 pre-test:
 # This one file does not get its paths replaced correctly in post-patch.
 	${REINPLACE_CMD} 's|"/etc"|"${ETCDIR:H}"|g' \
 		${WRKSRC}/test/units/playbook/test_helpers.py
 # This test constructs a Python script inline and uses an invalid path to it.
 	${REINPLACE_CMD} 's|/usr/bin/python|${PYTHON_CMD}|' \
 		${WRKSRC}/test/units/modules/test_async_wrapper.py
 # Skip the SELinux tests, it's not present on FreeBSD.
 	${RM} ${WRKSRC}/test/units/module_utils/basic/test_selinux.py
 # Disable some failing tests. They fail to detect that emoji are of width 2 istead of 1.
 	${RM} ${WRKSRC}/test/units/utils/test_display.py
 
 .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}
diff --git a/www/onionbalance/Makefile b/www/onionbalance/Makefile
index 3543924fdf31..0580ee109111 100644
--- a/www/onionbalance/Makefile
+++ b/www/onionbalance/Makefile
@@ -1,25 +1,28 @@
 PORTNAME=	onionbalance
 PORTVERSION=	0.2.1
 CATEGORIES=	www python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	OnionBalance-${PORTVERSION}
 
 MAINTAINER=	egypcio@FreeBSD.org
 COMMENT=	Load-balancing and Redundancy for Onion Services
 
 LICENSE=	GPLv3
 LICENSE_FILE=	${WRKSRC}/COPYING
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}future>=0:devel/py-future@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyaml>=0:textproc/py-pyaml@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>=0:security/py-pycrypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setproctitle>=0:devel/py-setproctitle@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools>=0:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}stem>=0:security/py-stem@${PY_FLAVOR} \
 		tor:security/tor
 
 USES=		python:3.6+
 USE_PYTHON=	autoplist distutils
 
 .include <bsd.port.mk>
diff --git a/www/onionshare/Makefile b/www/onionshare/Makefile
index cebeb8768830..67c37bd5aa01 100644
--- a/www/onionshare/Makefile
+++ b/www/onionshare/Makefile
@@ -1,32 +1,35 @@
 PORTNAME=	onionshare
 DISTVERSIONPREFIX=	v
 DISTVERSION=	2.2
 PORTREVISION=	7
 CATEGORIES=	www python security
 
 MAINTAINER=	egypcio@FreeBSD.org
 COMMENT=	Secure and anonymous file sharing via Tor
 
 LICENSE=	GPLv3
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 RUN_DEPENDS=	tor:security/tor \
 		obfs4proxy:security/obfs4proxy-tor \
 		${PYTHON_PKGNAMEPREFIX}Flask>=0:www/py-flask@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}Flask-HTTPAuth>=0:security/py-flask-httpauth@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>=0:security/py-pycrypto@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pysocks>=0:net/py-pysocks@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>=0:www/py-requests@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}stem>=0:security/py-stem@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>=0:devel/py-pytest@${PY_FLAVOR}
 
 USES=		cpe python:3.5+ pyqt:5
 USE_GITHUB=	yes
 GH_ACCOUNT=	micahflee
 USE_PYQT=	pyqt5 sip
 USE_PYTHON=	distutils autoplist noflavors
 
 post-patch:
 	@${REINPLACE_CMD} -e 's|/usr/local|${PREFIX}|g' ${WRKSRC}/onionshare/common.py
 
 .include <bsd.port.mk>
diff --git a/www/py-pyjwt1/Makefile b/www/py-pyjwt1/Makefile
index 61b79e3e4973..7a8d87e21b8c 100644
--- a/www/py-pyjwt1/Makefile
+++ b/www/py-pyjwt1/Makefile
@@ -1,35 +1,38 @@
 PORTNAME=	pyjwt1
 PORTVERSION=	1.7.1
 CATEGORIES=	www python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	PyJWT-${PORTVERSION}
 
 MAINTAINER=	terje@elde.net
 COMMENT=	JSON Web Token implementation in Python
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-pycrypto
+EXPIRATION_DATE=2022-09-30
+
 # Some tests are skipped without pycrypto, but its not
 # referenced as a requirement anymore.
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}cryptography>0:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pycrypto>=0:security/py-pycrypto@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	distutils concurrent autoplist
 
 CONFLICTS_INSTALL=	${PYTHON_PKGNAMEPREFIX}-pyjwt
 
 OPTIONS_DEFINE=	RSASSA
 
 RSASSA_DESC=		RSASSA-PKCS1 v1.5 signature support
 RSASSA_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cryptography>0:security/py-cryptography@${PY_FLAVOR}
 
 NO_ARCH=	yes
 
 do-test:
 	@cd ${WRKSRC} && ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest -v -rs -o addopts=
 
 .include <bsd.port.mk>