diff --git a/mail/mailman3/Makefile b/mail/mailman3/Makefile
index aebacdbf8f99..3e14fb2d40b6 100644
--- a/mail/mailman3/Makefile
+++ b/mail/mailman3/Makefile
@@ -1,6 +1,5 @@
 PORTNAME=	mailman
-PORTVERSION=	3.3.1
-PORTREVISION=	1
+PORTVERSION=	3.3.5
 CATEGORIES=	mail
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -11,22 +10,27 @@ COMMENT=	GNU Mailing List Management System, Core
 LICENSE=	GPLv3+
 
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}aiosmtpd>=1.1:mail/py-aiosmtpd@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}alembic14>0:databases/py-alembic14@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}alembic16>=1.6.2:databases/py-alembic16@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}atpublic>0:devel/py-atpublic@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click>0:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}dnspython>=1.14.0:dns/py-dnspython@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}falcon>=1.0.0.rc1:www/py-falcon@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}flufl.bounce>0:mail/py-flufl.bounce@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}flufl.i18n>=2.0:devel/py-flufl.i18n@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}flufl.lock>=3.1:devel/py-flufl.lock@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}falcon>=3.0.0:www/py-falcon@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}flufl.bounce>=4.0:mail/py-flufl.bounce@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}flufl.i18n>=3.2:devel/py-flufl.i18n@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}flufl.lock>=5.2:devel/py-flufl.lock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}lazr.config>0:devel/py-lazr.config@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}passlib>0:security/py-passlib@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>0:www/py-requests@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}sqlalchemy12>1.2.3:databases/py-sqlalchemy12@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}zope.component>0:devel/py-zope.component@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}zope.configuration>0:devel/py-zope.configuration@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}zope.event>0:devel/py-zope.event@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}zope.interface>0:devel/py-zope.interface@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}zope.interface>0:devel/py-zope.interface@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}importlib-resources>0:devel/py-importlib-resources@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}attrs>0:devel/py-attrs@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}gunicorn>0:www/py-gunicorn@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}psutil>0:sysutils/py-psutil@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}authres>0:mail/py-authres@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}authheaders>0:mail/py-authheaders@${PY_FLAVOR}
 
 USES=		cpe python:3.5+
 CPE_VENDOR=	gnu
diff --git a/mail/mailman3/distinfo b/mail/mailman3/distinfo
index f6f92216062a..a2c2063ee0f0 100644
--- a/mail/mailman3/distinfo
+++ b/mail/mailman3/distinfo
@@ -1,3 +1,3 @@
 TIMESTAMP = 1590347054
-SHA256 (mailman-3.3.1.tar.gz) = b8cfa4b50453abf2b499b272db17c25865d81a49208c43b004ec4989c88eae45
-SIZE (mailman-3.3.1.tar.gz) = 1184548
+SHA256 (mailman-3.3.5.tar.gz) = 9fb38d9b516d9fdeb9c9f961a7630330cda46c490b91defc94b2c16683eeaf8a 
+SIZE (mailman-3.3.5.tar.gz) = 1771305
diff --git a/mail/mailman3/files/patch-src_mailman_rest_tests_test__systemconf.py b/mail/mailman3/files/patch-src_mailman_rest_tests_test__systemconf.py
index 493874be02e3..d3899c69ad0c 100644
--- a/mail/mailman3/files/patch-src_mailman_rest_tests_test__systemconf.py
+++ b/mail/mailman3/files/patch-src_mailman_rest_tests_test__systemconf.py
@@ -1,11 +1,11 @@
---- src/mailman/rest/tests/test_systemconf.py.orig	2017-11-18 01:23:39 UTC
+--- src/mailman/rest/tests/test_systemconf.py.orig      2021-12-07 01:47:54 UTC
 +++ src/mailman/rest/tests/test_systemconf.py
-@@ -41,7 +41,7 @@ class TestSystemConfiguration(unittest.TestCase):
-             default_language='en',
-             email_commands_max_lines='10',
+@@ -48,7 +48,7 @@ class TestSystemConfiguration(unittest.TestCase):
+             filter_report='no',
              filtered_messages_are_preservable='no',
+             hold_digest='no',
 -            html_to_plain_text_command='/usr/bin/lynx -dump $filename',
 +            html_to_plain_text_command='/usr/local/bin/lynx -dump $filename',
              layout='testing',
              listname_chars='[-_.0-9a-z]',
-             noreply_address='noreply',
+             masthead_threshold='4',