diff --git a/devel/py-setuptools44/Makefile b/devel/py-setuptools44/Makefile
index 5ce729464799..69f8ec3bb218 100644
--- a/devel/py-setuptools44/Makefile
+++ b/devel/py-setuptools44/Makefile
@@ -1,52 +1,55 @@
 PORTNAME=	setuptools
 PORTVERSION=	44.1.1
 PORTREVISION=	2
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 PKGNAMESUFFIX=	44
 DIST_SUBDIR=	python
 
 # note: before committing to this port, contact portmgr to arrange for an
 # experimental ports run.  Untested commits may be backed out at portmgr's
 # discretion.
 MAINTAINER=	python@FreeBSD.org
 COMMENT=	Python packages installer
 WWW=		https://pypi.org/project/setuptools/
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Uses expired lang/python27
+EXPIRATION_DATE=	2026-11-01
+
 USES=		cpe python:2.7 zip
 USE_PYTHON=	allflavors autoplist concurrent distutils
 
 CPE_VENDOR=	python
 
 MAKE_ENV+=	SETUPTOOLS_DISABLE_VERSIONED_EASY_INSTALL_SCRIPT=1
 NO_ARCH=	yes
 PYDISTUTILS_SETUP=	${PYSETUP}
 
 PLIST_FILES=	"@sample %%PYTHON_SITELIBDIR%%/easy-install.pth.dist %%PYTHON_SITELIBDIR%%/easy-install.pth"
 
 .include <bsd.port.pre.mk>
 
 .if ${FLAVOR} != ${FLAVORS:[1]}
 SUB_FILES+=	pkg-message
 SUB_LIST+=	PYTHON_VER=${PYTHON_VER}
 .endif
 
 # These create dependency loops in redports/poudriere, because setuptools
 # is currently an explicit BUILD & RUN dependency in Uses/python.mk.
 #TEST_DEPENDS=  ${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR}
 #.if ${PYTHON_REL} < 30000
 #TEST_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR}
 #.endif
 # pkg install -y py38-pytest py38-mock py38-pytest-fixture-config py38-pytest-virtualenv py38-paver
 
 post-install:
 	${INSTALL_DATA} ${FILESDIR}/easy-install.pth.dist ${STAGEDIR}${PYTHON_SITELIBDIR}/
 
 do-test:
 	cd ${WRKSRC} && ${PYTHON_CMD} -m pytest -v -rs
 
 .include <bsd.port.post.mk>
diff --git a/mail/mailman/Makefile b/mail/mailman/Makefile
index 64fc99cd5a3b..f37708e94612 100644
--- a/mail/mailman/Makefile
+++ b/mail/mailman/Makefile
@@ -1,248 +1,251 @@
 PORTNAME=	mailman
 DISTVERSION=	2.1.39
 PORTREVISION=	4
 CATEGORIES=	mail
 MASTER_SITES=	GNU \
 		SF/${PORTNAME}/Mailman%202.1%20%28stable%29/${PORTVERSION} \
 		https://launchpad.net/mailman/${DISTVERSION:R}/${DISTVERSION}/+download/
 DIST_SUBDIR=	mailman
 
 PATCH_SITES=	LOCAL/mandree
 PATCH_DIST_STRIP=	-p1
 
 MAINTAINER=	mandree@FreeBSD.org
 COMMENT=	Mailing list manager with user-friendly web front-end
 WWW=		https://www.list.org/
 
 LICENSE=	GPLv2
 LICENSE_FILE=	${WRKSRC}/gnu-COPYING-GPL
 
+DEPRECATED=	Uses expired lang/python27
+EXPIRATION_DATE=	2026-11-01
+
 USES=		cpe fakeroot python:2.7 shebangfix tar:tgz
 CPE_VENDOR=	gnu
 
 USE_RC_SUBR=	mailman
 SHEBANG_FILES=	bin/msgfmt.py \
 		tests/fblast.py \
 		tests/onebounce.py
 
 GNU_CONFIGURE=	yes
 GNU_CONFIGURE_PREFIX=	${MAILMANDIR}
 CONFIGURE_ARGS+=--with-python=${PYTHON_CMD} \
 		--with-username=${MM_USERNAME} \
 		--with-groupname=${MM_GROUPNAME} \
 		--with-mail-gid=${MAIL_GID} --with-cgi-gid=${CGI_GID} \
 		--with-permcheck=no \
 		--with-mailhost=localhost \
 		--with-urlhost=localhost
 # setting these defeats the automated check for users in configure[.in], as of 2.1.39,
 # implemented in MM_FIND_* macros:
 CONFIGURE_ENV+=	CGI_GROUP=${CGI_GID} \
 		MAIL_GROUP=${MAIL_GID} \
 		MAILMAN_USER=${MM_USERNAME} \
 		MAILMAN_GROUP=${MM_GROUPNAME}
 
 CONFLICTS=	ja-mailman-2.1.* mailman*exim* mailman*postfix*
 
 # The Mailman port supports a number of variables that may be tweaked at
 # build time.  Getting the values of some of them right is crucial!
 #
 MM_USERNAME?=	mailman
 MM_USERID?=	91
 MM_GROUPNAME?=	${MM_USERNAME}
 MM_GROUPID?=	${MM_USERID}
 MM_DIR?=	mailman
 CGI_GID?=	www
 IMGDIR?=	www/icons
 #
 # End of user-configurable variables.
 
 USERS=		${MM_USERNAME}
 GROUPS=		${MM_GROUPNAME}
 
 MAILMANDIR=	${PREFIX}/${MM_DIR}
 PLIST_SUB=	MMDIR=${MM_DIR} IMGDIR=${IMGDIR} MM_USERNAME=${MM_USERNAME} MM_GROUPNAME=${MM_GROUPNAME}
 SUB_FILES=	pkg-message pkg-install mailman.newsyslog.sample
 SUB_LIST=	MAILMANDIR=${MAILMANDIR} USER=${MM_USERNAME} GROUP=${MM_GROUPNAME} PYTHON_CMD="${PYTHON_CMD}"
 PKGDEINSTALL=	${PKGINSTALL}
 
 PORTDOCS=	ACKNOWLEDGMENTS BUGS FAQ INSTALL NEWS README README-I18N.en \
 		README.CONTRIB README.NETSCAPE \
 		README.USERAGENT TODO UPGRADING \
 		mailman-admin.txt \
 		mailman-install.txt \
 		mailman-member.txt \
 		FreeBSD-post-install-notes
 
 OPTIONS_SINGLE=		MTA
 OPTIONS_SINGLE_MTA=	COURIER EXIM4 OPENSMTPD POSTFIX SENDMAIL
 OPTIONS_DEFINE=		HTDIG NAMAZU2 NOMAILPWD NLS DOCS
 OPTIONS_DEFAULT=	SENDMAIL NOMAILPWD
 COURIER_DESC=		for use with courier
 EXIM4_DESC=		for use with exim4
 EXIM4_RUN_DEPENDS=	exim>=0:mail/exim
 OPENSMTPD_DESC=		for use with opensmtpd - EXPERIMENTAL -
 POSTFIX_DESC=		for use with postfix
 POSTFIX_RUN_DEPENDS=	postfix:mail/postfix
 SENDMAIL_DESC=		for use with sendmail
 HTDIG_DESC=		- EXPERIMENTAL - htdig integration patches
 NAMAZU2_DESC=		Make private archives searchable with namazu2
 NOMAILPWD_DESC=		Elide plaintext passwords from monthly reminders
 MTA_DESC=		Integrate with which MTA?
 
 .include <bsd.port.options.mk>
 
 SUB_LIST+=	NLS="${PORT_OPTIONS:MNLS}"
 
 # enforce EXAMPLES option, necessary so that @sample
 # can install the newsyslog file
 .if empty(PORT_OPTIONS:MEXAMPLES)
 PORT_OPTIONS+=	EXAMPLES
 .endif
 
 .if ${PORT_OPTIONS:MNLS}
 USES+=		gettext
 PLIST_SUB+=	NLS=""
 .else
 PLIST_SUB+=	NLS="@comment "
 MAKE_ARGS+=	LANGUAGES=en
 .endif
 
 .if ${PORT_OPTIONS:MSENDMAIL}
 MAIL_GID?=	mailnull
 .endif
 
 .if ${PORT_OPTIONS:MEXIM4}
 MAIL_GID?=	mail
 .endif
 
 .if ${PORT_OPTIONS:MPOSTFIX}
 MAIL_GID?=	mailman
 EXTRA_PATCHES+=	${FILESDIR}/postfix-verp.diff
 .endif
 
 .if ${PORT_OPTIONS:MCOURIER}
 MAIL_GID?=	courier
 .endif
 
 .if ${PORT_OPTIONS:MOPENSMTPD}
 MAIL_GID?=	_smtpd
 .endif
 
 .if ${PORT_OPTIONS:MHTDIG}
 # no whitespace here!
 PKGNAMESUFFIX:=	${PKGNAMESUFFIX}-with-htdig
 # how to create PATCHFILES:
 #X identify what is the version of msapiro's patches corresponding to the release.
 #X fetch http://bazaar.launchpad.net/~msapiro/mailman/htdig/tarball/1822
 #X unpack this tarball, and the original distfile
 #X diff -NEur original-unpack bazaar-unpack | xz --best -c >msapiro-htdig-1822.patch.xz
 #X upload the latter with mode 0644 or similar to freefall's public_distfiles/ directory
 _HTDIGREV=	1822
 PATCHFILES+=	msapiro-htdig-${_HTDIGREV}.patch.xz
 EXTRA_PATCHES+=	${FILESDIR}/mailman-htdig-xss.patch
 RUN_DEPENDS+=	htdig:textproc/htdig
 PLIST_SUB+=	SUB_HTDIG=""
 .else
 PLIST_SUB+=	SUB_HTDIG="@comment "
 .endif
 
 .if ${PORT_OPTIONS:MNAMAZU2}
 RUN_DEPENDS+=	mknmz:databases/namazu2
 EXTRA_PATCHES+=	${FILESDIR}/extra-patch-Mailman-Cgi-private.py
 .endif
 
 .if ${PORT_OPTIONS:MNOMAILPWD}
 EXTRA_PATCHES+=	${FILESDIR}/extra-patch-mailpasswds
 .endif
 
 BUILD_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}dnspython1>=0:dns/py-dnspython1@${PY_FLAVOR}
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}dnspython1>=0:dns/py-dnspython1@${PY_FLAVOR}
 
 pre-everything::
 	@${ECHO} ""
 	@${ECHO} "You may change the following build options:"
 	@${ECHO} ""
 	@${ECHO} "Option		Default Value	Description"
 	@${ECHO} "-------------	---------------	------------------------------------------------"
 	@${ECHO} "MM_USERNAME	mailman		The username of the Mailman user."
 	@${ECHO} "MM_USERID	91		The user ID of the Mailman user."
 	@${ECHO} "MM_GROUPNAME	mailman		The group to which the Mailman user will belong."
 	@${ECHO} "MM_GROUPID	\$$MM_USERID	The group ID for the Mailman user."
 	@${ECHO} "MM_DIR		mailman		Mailman will be installed in"
 	@${ECHO} "				${PREFIX}/${MM_DIR}."
 	@${ECHO} "CGI_GID		www		The group name or id under which your web"
 	@${ECHO} "				server executes CGI scripts."
 	@${ECHO} "IMGDIR		www/icons	Icon images will be installed in"
 	@${ECHO} "				${PREFIX}/${IMGDIR}."
 	@${ECHO} ""
 
 post-patch:
 	${REINPLACE_CMD} -e 's#%%LOCALBASE%%#${LOCALBASE}#g' \
 	  ${WRKSRC}/Mailman/Defaults.py.in
 	${REINPLACE_CMD} -e 's/^0,5,10/#&/' ${WRKSRC}/cron/crontab.in.in
 .if empty(PORT_OPTIONS:MNLS)
 	${REINPLACE_CMD} -e 's/messages//' ${WRKSRC}/Makefile.in
 .endif
 	${MV} ${WRKSRC}/configure.in ${WRKSRC}/configure.ac # suppress warning
 
 # post-patch-HTDIG-on is to fix https://bugs.freebsd.org/bugzilla/show_bug.cgi?id=238508
 post-patch-HTDIG-on:
 	# these should match those in ht://Dig's ${LOCALBASE}/bin/rundig
 	${REINPLACE_CMD} -E \
 		-e 's#^(DBDIR)=/opt/www/var/htdig#\1=${LOCALBASE}/share/htdig/database#' \
 		-e 's#^(COMMONDIR)=/opt/www/share/htdig#\1=${LOCALBASE}/share/htdig/common#' \
 		-e 's#^(BINDIR)=/opt/www/bin#\1=${LOCALBASE}/bin#' \
 		-e 's#^(conffile)=/opt/www/conf/#\1=${LOCALBASE}/etc/htdig/#' \
 		${WRKSRC}/cron/rundig
 	${REINPLACE_CMD} -E \
 		-e 's#/opt/www/htdig/bin#${LOCALBASE}/bin#' \
 		${WRKSRC}/Mailman/Cgi/remote?mmsearch
 
 .if ${PORT_OPTIONS:MPOSTFIX}
 pre-configure:
 	${ECHO} "MTA = 'Postfix'" >> ${WRKSRC}/Mailman/mm_cfg.py.dist.in
 .endif
 
 post-install:
 	${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
 	${INSTALL_DATA} ${WRKDIR}/mailman.newsyslog.sample ${STAGEDIR}${EXAMPLESDIR}
 .for i in admindb admin confirm create edithtml listinfo options private \
 	rmlist roster subscribe
 	${STRIP_CMD} ${STAGEDIR}${MAILMANDIR}/cgi-bin/${i}
 .endfor
 .if ${PORT_OPTIONS:MHTDIG}
 .for i in htdig mmsearch
 	${STRIP_CMD} ${STAGEDIR}${MAILMANDIR}/cgi-bin/${i}
 .endfor
 .endif
 	${STRIP_CMD} ${STAGEDIR}${MAILMANDIR}/mail/mailman
 # Compile additional Python scripts:
 .for dir in bin
 	(cd ${STAGEDIR}${MAILMANDIR} \
 	    && ${PYTHON_CMD} ${PYTHON_LIBDIR}/compileall.py \
 	    -d ${MAILMANDIR}/${dir} ${dir})
 .endfor
 	@${RM} ${STAGEDIR}${MAILMANDIR}/pythonlib/*.egg-info
 	@${RM} ${STAGEDIR}${MAILMANDIR}/Mailman/mm_cfg.py
 	@${RM} ${STAGEDIR}${MAILMANDIR}/Mailman/mm_cfg.pyc
 	@${MKDIR} ${STAGEDIR}${PREFIX}/${IMGDIR}
 	${CP} -p ${STAGEDIR}${MAILMANDIR}/icons/* ${STAGEDIR}${PREFIX}/${IMGDIR}
 	${INSTALL_DATA} ${FILESDIR}/powerlogo.png \
 	  ${STAGEDIR}${PREFIX}/${IMGDIR}/
 	${INSTALL_DATA} ${FILESDIR}/powerlogo.png \
 	  ${STAGEDIR}${MAILMANDIR}/icons/
 .if ${PORT_OPTIONS:MDOCS}
 	${CP} -R ${WRKSRC}/doc/* ${WRKSRC}/
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	${INSTALL_DATA} ${FILESDIR}/FreeBSD-post-install-notes ${STAGEDIR}${DOCSDIR}
 .for docfile in ${PORTDOCS:NFreeBSD-post-install-notes}
 	${INSTALL_DATA} ${WRKSRC}/${docfile} ${STAGEDIR}${DOCSDIR}
 .endfor
 .endif
 	@${MKDIR} ${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 	${ECHO} "This marker file ensures that Python's upgrade-site-packages handles ${PKGNAME}." >${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}/mailman-info.txt
 	${INSTALL_SCRIPT} ${PKGINSTALL} ${STAGEDIR}${MAILMANDIR}/bin/FreeBSD-post-install
 	${MKDIR} ${STAGEDIR}${MAILMANDIR}/templates/site/en
 	${INSTALL_DATA} ${FILESDIR}/templates_site_README.txt ${STAGEDIR}${MAILMANDIR}/templates/site/README.txt
 
 .include <bsd.port.mk>
diff --git a/www/moinmoin/Makefile b/www/moinmoin/Makefile
index c3a5a64401b9..f2ed30c5ddc3 100644
--- a/www/moinmoin/Makefile
+++ b/www/moinmoin/Makefile
@@ -1,90 +1,93 @@
 PORTNAME=	moinmoin
 PORTVERSION=	1.9.11
 PORTREVISION=	1
 CATEGORIES=	www python
 MASTER_SITES=	https://static.moinmo.in/files/
 DISTNAME=	moin-${PORTVERSION}
 
 MAINTAINER=	wiki-admin@FreeBSD.org
 COMMENT=	Easy to use, full-featured and extensible wiki software package
 WWW=		https://moinmo.in/
 
 LICENSE=	GPLv2
 LICENSE_FILE=	${WRKSRC}/docs/licenses/COPYING
 
+DEPRECATED=	Uses expired lang/python27
+EXPIRATION_DATE=	2026-11-01
+
 USES=		cpe python:2.7 shebangfix
 USE_PYTHON=	distutils
 
 NO_ARCH=	yes
 CPE_VENDOR=	moinmo
 PYDISTUTILS_PKGNAME=	moin
 SHEBANG_FILES=	wiki/server/moin*
 
 PLIST_SUB+=	PYTHON_SITELIB=${PYTHON_SITELIBDIR:S|^${LOCALBASE}/||} \
 		DATADIR=share/moin
 SUB_FILES=	pkg-install
 SUB_LIST=	MOINDIR=${MOINDIR} MOINDEST=${MOINDEST} MOINVER=${MOINVER} \
 		HTDOCS=${PYTHON_SITELIBDIR}/MoinMoin/web/static/htdocs
 
 OPTIONS_DEFINE=		RECAPTCHA VERIFYEMAIL
 OPTIONS_DEFAULT=	RECAPTCHA VERIFYEMAIL
 OPTIONS_SUB=		yes
 
 RECAPTCHA_DESC=		reCAPTCHA v2 support
 VERIFYEMAIL_DESC=	Support for verifying new account email addresses
 
 RECAPTCHA_EXTRA_PATCHES=	${PATCHDIR}/extra-patch-recaptchav2
 VERIFYEMAIL_EXTRA_PATCHES=	${PATCHDIR}/extra-patch-verifyemail
 
 CGIUSER?=	www
 CGIGROUP?=	www
 MOINDIR=	${PREFIX}/share/moin
 MOINDEST?=	${PREFIX}/www/wiki
 MOINVER?=	${PORTVERSION:S|.||g}
 MOINTYPE?=	CGI
 
 PKGDEINSTALL=	${PKGINSTALL}
 
 .if ${MOINTYPE} == "STANDALONE"
 MOINSCRIPT=	${MOINDIR}/server/moin
 .elif ${MOINTYPE} == "FCGI"
 MOINSCRIPT=	${MOINDIR}/server/moin.fcgi
 .elif ${MOINTYPE} == "MOD_PYTHON"
 .elif ${MOINTYPE} == "CGI"
 MOINSCRIPT=	${MOINDIR}/server/moin.cgi
 .elif ${MOINTYPE} == "WSGI"
 MOINSCRIPT=	${MOINDIR}/server/moin.wsgi
 .else
 BROKEN=		MOINTYPE must be a STANDALONE, FCGI, WSGI, MOD_PYTHON, or CGI
 .endif
 
 pre-everything::
 	@${ECHO}
 	@${ECHO} "Set MOINTYPE=(CGI|FCGI|WSGI|STANDALONE) to define"
 	@${ECHO} "type of installation. Default is CGI."
 	@${ECHO} "Use MOINDEST=/path to modify installation destination."
 	@${ECHO} "Default value for MOINDEST is ${PREFIX}/www/wiki."
 	@${ECHO}
 	@${ECHO} "To get correct permissions, please set CGIUSER, CGIGROUP"
 	@${ECHO} "per default it is set to www:www."
 	@${ECHO}
 
 instance: pre-everything apply-slist
 	@${ECHO_CMD} "Creating a new wiki instance in ${MOINDEST}."; \
 	if [ -f ${MOINDIR}/config/wikiconfig.py ]; then \
 		${MKDIR} ${MOINDEST}; \
 		${CP} -R ${MOINDIR}/data ${MOINDEST}; \
 		${CP} -R ${MOINDIR}/underlay ${MOINDEST}; \
 		${CHMOD} -R u+rw,go-ws ${MOINDEST}/data; \
 		${INSTALL_SCRIPT} ${MOINDIR}/config/wikiconfig.py ${MOINDEST}; \
 		if [ ! -z ${MOINSCRIPT} ]; then \
 			${INSTALL_SCRIPT} ${MOINSCRIPT} ${MOINDEST}; \
 		fi; \
 		${CHOWN} -R ${CGIUSER}:${CGIGROUP} ${MOINDEST}; \
 		${SH} ${PKGINSTALL} ${PKGNAME} INSTANCE ${MOINTYPE}; \
 	else \
 		${ECHO_CMD} "You need to install moinmoin first before trying"; \
 		${ECHO_CMD} "to add a new wiki instance."; \
 	fi
 
 .include <bsd.port.mk>