diff --git a/databases/datasette/Makefile b/databases/datasette/Makefile
index 7b747832e099..991530b4abc5 100644
--- a/databases/datasette/Makefile
+++ b/databases/datasette/Makefile
@@ -1,41 +1,44 @@
 PORTNAME=	datasette
 DISTVERSION=	0.65.1
 CATEGORIES=	databases www
 MASTER_SITES=	PYPI
 
 MAINTAINER=	yuri@FreeBSD.org
 COMMENT=	Multi-tool for exploring and publishing data
 WWW=		https://datasette.io \
 		https://github.com/simonw/datasette
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired devel/py-pytest-runner
+EXPIRATION_DATE=2025-06-01
+
 PY_DEPENDS=	\
 		${PYTHON_PKGNAMEPREFIX}aiofiles>=0.4:devel/py-aiofiles@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}asgi-csrf>=0.9:www/py-asgi-csrf@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}asgiref>=3.2.10:www/py-asgiref@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click>=7.1.1:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click-default-group-wheel>=1.2.2:devel/py-click-default-group-wheel@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}hupper>=1.9:devel/py-hupper@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}janus>=0.6.2:devel/py-janus@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}Jinja2>=2.10.3:devel/py-Jinja2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}httpx>=0.20:www/py-httpx@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}itsdangerous>=1.1:security/py-itsdangerous@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mergedeep>=1.1.1:devel/py-mergedeep@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pint>=0.9:devel/py-pint@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pluggy>=1.0:devel/py-pluggy@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}uvicorn>=0.11:www/py-uvicorn@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyyaml>=5.3:devel/py-pyyaml@${PY_FLAVOR}
 BUILD_DEPENDS=	${PY_DEPENDS} \
 		${PYTHON_PKGNAMEPREFIX}pip>0:devel/py-pip@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-runner>0:devel/py-pytest-runner@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PY_DEPENDS}
 
 USES=		python
 USE_PYTHON=	distutils autoplist
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/sysutils/iocage-devel/Makefile b/sysutils/iocage-devel/Makefile
index 3acae194b367..628ce5febc40 100644
--- a/sysutils/iocage-devel/Makefile
+++ b/sysutils/iocage-devel/Makefile
@@ -1,59 +1,62 @@
 PORTNAME=	iocage-devel
 PORTVERSION=	1.10.20250103
 PORTREVISION=	1
 PORTEPOCH=	1
 CATEGORIES=	sysutils python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	nc@FreeBSD.org
 COMMENT=	FreeBSD jail manager written in Python3
 WWW=		https://github.com/freebsd/iocage
 
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired devel/py-pytest-runner
+EXPIRATION_DATE=2025-06-01
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}click>=6.7:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}coloredlogs>0:devel/py-coloredlogs@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}dnspython>0:dns/py-dnspython@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}gitpython>=2.1.10:devel/py-gitpython@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}jsonschema>0:devel/py-jsonschema@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}libzfs>=1.0.2:filesystems/py-libzfs@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}netifaces>0:net/py-netifaces@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-runner>=2.0.0:devel/py-pytest-runner@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>=2.11.1:www/py-requests@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}six>0:devel/py-six@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}texttable>=0.8.7:textproc/py-texttable@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tqdm>=4.10.0:misc/py-tqdm@${PY_FLAVOR} \
 		ca_root_nss>0:security/ca_root_nss
 
 USES=		python
 USE_GITHUB=	yes
 GH_ACCOUNT=	freebsd
 GH_PROJECT=	iocage
 GH_TAGNAME=	c55e05aebb305b4013554ec80298113c50d1c74c
 
 USE_PYTHON=	autoplist distutils
 
 CONFLICTS=	py*-iocage py*-iocage-devel
 NO_ARCH=	yes
 
 _IOCAGE_LIB_VERSION=	1.10
 PLIST_FILES=		${PYTHON_SITELIBDIR}/${PORTNAME:S/-devel//g}_lib-${_IOCAGE_LIB_VERSION}-py${PYTHON_VER}.egg-info/dependency_links.txt \
 			${PYTHON_SITELIBDIR}/${PORTNAME:S/-devel//g}_lib-${_IOCAGE_LIB_VERSION}-py${PYTHON_VER}.egg-info/entry_points.txt \
 			${PYTHON_SITELIBDIR}/${PORTNAME:S/-devel//g}_lib-${_IOCAGE_LIB_VERSION}-py${PYTHON_VER}.egg-info/PKG-INFO \
 			${PYTHON_SITELIBDIR}/${PORTNAME:S/-devel//g}_lib-${_IOCAGE_LIB_VERSION}-py${PYTHON_VER}.egg-info/requires.txt \
 			${PYTHON_SITELIBDIR}/${PORTNAME:S/-devel//g}_lib-${_IOCAGE_LIB_VERSION}-py${PYTHON_VER}.egg-info/SOURCES.txt \
 			${PYTHON_SITELIBDIR}/${PORTNAME:S/-devel//g}_lib-${_IOCAGE_LIB_VERSION}-py${PYTHON_VER}.egg-info/top_level.txt \
 			${PYTHON_SITELIBDIR}/${PORTNAME:S/-devel//g}_lib/plugin_manifest.json
 
 OPTIONS_DEFAULT=		GIT
 OPTIONS_RADIO=			GIT_PACKAGE
 OPTIONS_RADIO_GIT_PACKAGE=	GIT GIT_LITE
 
 GIT_DESC=	depend on devel/git
 GIT_LITE_DESC=	depend on lite flavor of devel/git (bare minimum git experience)
 
 GIT_RUN_DEPENDS=	git:devel/git
 GIT_LITE_RUN_DEPENDS=	git:devel/git@lite
 
 .include <bsd.port.mk>