diff --git a/deskutils/calcurse/Makefile b/deskutils/calcurse/Makefile
index 051c96d88b27..8c6de164c942 100644
--- a/deskutils/calcurse/Makefile
+++ b/deskutils/calcurse/Makefile
@@ -1,44 +1,47 @@
 PORTNAME=	calcurse
 DISTVERSION=	4.8.1
 PORTREVISION=	1
 CATEGORIES=	deskutils
 MASTER_SITES=	https://calcurse.org/files/ \
 		https://fossies.org/linux/privat/
 
 MAINTAINER=	eduardo@FreeBSD.org
 COMMENT=	Text-based calendar and scheduling application
 WWW=		https://calcurse.org/
 
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/COPYING
 
+DEPRECATED=	Depends on expired security/py-oauth2client
+EXPIRATION_DATE=2025-06-01
+
 USES=		ncurses shebangfix
 SHEBANG_FILES=	contrib/caldav/calcurse-caldav \
 		contrib/caldav/calcurse-caldav.py \
 		contrib/vdir/calcurse-vdir \
 		contrib/vdir/calcurse-vdir.py
 GNU_CONFIGURE=	yes
 CONFIGURE_ARGS=	--without-asciidoc
 
 OPTIONS_DEFINE=		CALDAV DOCS NLS
 OPTIONS_DEFAULT=	CALDAV
 OPTIONS_SUB=		yes
 
 CALDAV_DESC=	Support Calendaring Extensions to WebDAV
 
 CALDAV_USES=		python
 CALDAV_USES_OFF=	python:env
 CALDAV_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}httplib2>=0:www/py-httplib2@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}oauth2client>=0:security/py-oauth2client@${PY_FLAVOR}
 
 DOCS_USES=		gmake
 DOCS_CONFIGURE_ENABLE=	docs
 
 NLS_USES=		gettext
 NLS_CONFIGURE_ENABLE=	nls
 
 post-patch:
 	@${REINPLACE_CMD} -e 's|^docdir = .*|docdir = ${DOCSDIR}|' ${WRKSRC}/doc/Makefile.in
 	@${REINPLACE_CMD} -e 's|-R$$found_dir||' ${WRKSRC}/configure
 
 .include <bsd.port.mk>
diff --git a/deskutils/gcalcli/Makefile b/deskutils/gcalcli/Makefile
index 26b7d6af2402..cf0c79e04dc1 100644
--- a/deskutils/gcalcli/Makefile
+++ b/deskutils/gcalcli/Makefile
@@ -1,36 +1,39 @@
 PORTNAME=	gcalcli
 PORTVERSION=	4.0.4
 DISTVERSIONPREFIX=	v
 PORTREVISION=	4
 CATEGORIES=	deskutils python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	ports@thelanman.net
 COMMENT=	Google Calendar Command Line Interface
 WWW=		https://github.com/insanum/gcalcli
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-oauth2client
+EXPIRATION_DATE=2025-06-01
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}python-dateutil>=0:devel/py-python-dateutil@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}google-api-python-client>=1.4:www/py-google-api-python-client@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}httplib2>=0:www/py-httplib2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}parsedatetime>=0:devel/py-parsedatetime@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}oauth2client>0:security/py-oauth2client@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}six>0:devel/py-six@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist concurrent distutils
 
 USE_GITHUB=	yes
 GH_ACCOUNT=	insanum
 
 NO_ARCH=	yes
 
 OPTIONS_DEFINE=		ICS_VCAL
 OPTIONS_DEFAULT=	ICS_VCAL
 
 ICS_VCAL_DESC=		Enable importing of ics/vcal files
 ICS_VCAL_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}vobject>=0.4.8:deskutils/py-vobject@${PY_FLAVOR}
 
 .include <bsd.port.mk>
diff --git a/www/py-pydrive2/Makefile b/www/py-pydrive2/Makefile
index f3d0204ab647..f8cb93e58b84 100644
--- a/www/py-pydrive2/Makefile
+++ b/www/py-pydrive2/Makefile
@@ -1,58 +1,61 @@
 PORTNAME=	PyDrive2
 DISTVERSION=	1.21.3
 CATEGORIES=	www python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	pydrive2-${DISTVERSION}
 
 MAINTAINER=	matthew@wener.org
 COMMENT=	PyDrive2 is a wrapper library of google-api-python-client
 WWW=		https://github.com/iterative/PyDrive2
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired security/py-oauth2client
+EXPIRATION_DATE=2025-06-01
+
 BUILD_DEPENDS=	${PY_SETUPTOOLS} \
 		${PYTHON_PKGNAMEPREFIX}setuptools-scm>=0:devel/py-setuptools-scm@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}google-api-python-client>=0:www/py-google-api-python-client@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}oauth2client>=0:security/py-oauth2client@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}openssl<=24.2.1,1:security/py-openssl@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyyaml>=0:devel/py-pyyaml@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist cryptography pep517
 
 NO_ARCH=	yes
 
 PORTDOCS=	*
 PORTEXAMPLES=	*
 
 OPTIONS_DEFINE=	DOCS EXAMPLES FSSPEC
 
 FSSPEC_DESC=		Filesystem interfaces for Python
 
 DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}furo>0:textproc/py-furo@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}sphinx>=0:textproc/py-sphinx@${PY_FLAVOR}
 FSSPEC_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}appdirs>=0:devel/py-appdirs@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}fsspec>=0:filesystems/py-fsspec@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}funcy>=0:devel/py-funcy@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}tqdm>=0:misc/py-tqdm@${PY_FLAVOR}
 
 pre-build-DOCS-on:
 	@(cd ${BUILD_WRKSRC}; \
 	${SETENVI} ${WRK_ENV} \
 	sphinx-build-${PYTHON_VER} \
 		-b html -d _build/doctress docs/ build/sphinx/html)
 
 do-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	(cd ${WRKSRC}/build/sphinx/html && \
 		${COPYTREE_SHARE} . ${STAGEDIR}${DOCSDIR} \
 		"! -name .buildinfo -and ! -name .nojekyll -and ! -name objects.inv")
 
 do-install-EXAMPLES-on:
 	${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
 	(cd ${WRKSRC}/examples && ${COPYTREE_SHARE} . ${STAGEDIR}${EXAMPLESDIR})
 
 .include <bsd.port.mk>