diff --git a/deskutils/py-todoman/Makefile b/deskutils/py-todoman/Makefile
index 0c83ab7db629..a0767fa5c9d5 100644
--- a/deskutils/py-todoman/Makefile
+++ b/deskutils/py-todoman/Makefile
@@ -1,42 +1,41 @@
 PORTNAME=	todoman
-DISTVERSION=	3.9.0
+DISTVERSION=	4.0.0
 CATEGORIES=	deskutils python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	andreas@bilke.org
 COMMENT=	Simple CalDAV-based todo manager
 
 LICENSE=	ISCL
 LICENSE_FILE=	${WRKSRC}/LICENCE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools_scm>0:devel/py-setuptools_scm@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}atomicwrites>0:devel/py-atomicwrites@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click-log>=0.2.1:devel/py-click-log@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}click>=7.1<8.0:devel/py-click@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}configobj>0:devel/py-configobj@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}click>=7.1<9.0:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}dateutil>0:devel/py-dateutil@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}humanize>0:devel/py-humanize@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}icalendar>=4.0.3:devel/py-icalendar@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}parsedatetime>0:devel/py-parsedatetime@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tabulate>0:devel/py-tabulate@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}urwid>0:devel/py-urwid@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}vdirsyncer>0:deskutils/py-vdirsyncer@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}xdg>0:devel/py-xdg@${PY_FLAVOR}
 
-USES=		python:3.5+
+USES=		python:3.8+
 USE_PYTHON=	autoplist concurrent distutils
 
 NO_ARCH=	yes
 
-PLIST_FILES=	${EXAMPLESDIR}/todoman.conf.sample \
+PLIST_FILES=	${EXAMPLESDIR}/config.py.sample \
 		share/zsh/site-functions/_todoman
 
 post-install:
 	@${MKDIR} ${STAGEDIR}${PREFIX}/share/zsh/site-functions
 	${INSTALL_DATA} ${WRKSRC}/contrib/completion/zsh/_todo \
 		${STAGEDIR}${PREFIX}/share/zsh/site-functions/_todoman
 	${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
-	(cd ${WRKSRC}/ && ${COPYTREE_SHARE} todoman.conf.sample ${STAGEDIR}${EXAMPLESDIR})
+	(cd ${WRKSRC}/ && ${COPYTREE_SHARE} config.py.sample ${STAGEDIR}${EXAMPLESDIR})
 
 .include <bsd.port.mk>
diff --git a/deskutils/py-todoman/distinfo b/deskutils/py-todoman/distinfo
index d9e875a35796..3481a8579c17 100644
--- a/deskutils/py-todoman/distinfo
+++ b/deskutils/py-todoman/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1607109164
-SHA256 (todoman-3.9.0.tar.gz) = e7e5cab13ecce0562b1f13f46ab8cbc079caed4b462f2371929f8a4abff2bcbe
-SIZE (todoman-3.9.0.tar.gz) = 62813
+TIMESTAMP = 1621520139
+SHA256 (todoman-4.0.0.tar.gz) = 4c4d0c6533da8d553f3dd170c9c4ff3752eb11fd7177ee391414a39adfef60ad
+SIZE (todoman-4.0.0.tar.gz) = 65974
diff --git a/deskutils/py-todoman/pkg-message b/deskutils/py-todoman/pkg-message
new file mode 100644
index 000000000000..f357019b9707
--- /dev/null
+++ b/deskutils/py-todoman/pkg-message
@@ -0,0 +1,9 @@
+[
+{ type: install
+  message: <<EOM
+The config file format changed from version 3 to 4.
+
+See https://github.com/pimutils/todoman/blob/v4.0.0/CHANGELOG.rst
+EOM
+}
+]