diff --git a/devel/py-pcodedmp/Makefile b/devel/py-pcodedmp/Makefile
index c9215cb58ac3..da16010fda14 100644
--- a/devel/py-pcodedmp/Makefile
+++ b/devel/py-pcodedmp/Makefile
@@ -1,24 +1,27 @@
 PORTNAME=	pcodedmp
 PORTVERSION=	1.2.6
 PORTREVISION=	1
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	VBA p-code disassembler
 WWW=		https://github.com/bontchev/pcodedmp
 
 LICENSE=	GPLv3
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Depends on expired devel/py-oletools
+EXPIRATION_DATE=2025-06-01
+
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=0:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}oletools>=0.54:devel/py-oletools@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist concurrent pep517
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/textproc/py-RTFDE/Makefile b/textproc/py-RTFDE/Makefile
index 1860e2f7a546..0f3622cdc2b1 100644
--- a/textproc/py-RTFDE/Makefile
+++ b/textproc/py-RTFDE/Makefile
@@ -1,22 +1,25 @@
 PORTNAME=	RTFDE
 DISTVERSION=	0.1.1
 PORTREVISION=	1
 CATEGORIES=	textproc python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	DtxdF@disroot.org
 COMMENT=	Library for extracting HTML content from RTF encapsulated HTML
 WWW=		https://github.com/seamustuohy/RTFDE
 
 LICENSE=	LGPL3
 
+DEPRECATED=	Depends on expired devel/py-oletools
+EXPIRATION_DATE=2025-06-01
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}lark>=0.11:devel/py-lark@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}oletools>=0.56:devel/py-oletools@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist distutils
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/textproc/py-extract-msg/Makefile b/textproc/py-extract-msg/Makefile
index 093f8f350d34..2514cc7974eb 100644
--- a/textproc/py-extract-msg/Makefile
+++ b/textproc/py-extract-msg/Makefile
@@ -1,31 +1,34 @@
 PORTNAME=	extract-msg
 DISTVERSION=	0.52.0
 PORTREVISION=	2
 CATEGORIES=	textproc python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	extract_msg-${PORTVERSION}
 
 MAINTAINER=	DtxdF@disroot.org
 COMMENT=	Extracts emails and attachments saved in MS Outlook's .msg files
 WWW=		https://github.com/TeamMsgExtractor/msg-extractor
 
 LICENSE=	GPLv3
 LICENSE_FILE=	${WRKSRC}/LICENSE.txt
 
+DEPRECATED=	Depends on expiring textproc/py-RTFDE
+EXPIRATION_DATE=2025-06-01
+
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}beautifulsoup>=4.11.1:www/py-beautifulsoup@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}chardet>=4.0.0:textproc/py-chardet@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}compressed-rtf>=1.0.6:archivers/py-compressed-rtf@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}ebcdic>=1.1.1:textproc/py-ebcdic@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}olefile>=0.46:devel/py-olefile@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytz-deprecation-shim>0:devel/py-pytz-deprecation-shim@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}red-black-tree-mod>=0:devel/py-red-black-tree-mod@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}RTFDE>=0.0.2:textproc/py-RTFDE@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tzlocal>=4.2:devel/py-tzlocal@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist distutils
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>