diff --git a/textproc/py-mkdocs/Makefile b/textproc/py-mkdocs/Makefile
index 136919bcf8f3..675ad419ab1c 100644
--- a/textproc/py-mkdocs/Makefile
+++ b/textproc/py-mkdocs/Makefile
@@ -1,36 +1,45 @@
 PORTNAME=	mkdocs
-DISTVERSION=	1.3.0
+DISTVERSION=	1.4.0
 CATEGORIES=	textproc python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	kai@FreeBSD.org
 COMMENT=	Project documentation with Markdown
 WWW=		https://www.mkdocs.org
 
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}click>=3.3:devel/py-click@${PY_FLAVOR} \
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}click>=7.0:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}ghp-import>=1.0:www/py-ghp-import@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}importlib-metadata>=4.3:devel/py-importlib-metadata@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}Jinja2>=2.10.2:devel/py-Jinja2@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}markdown>=3.2.1:textproc/py-markdown@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}Jinja2>=2.11.1:devel/py-Jinja2@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}markdown>=3.2.1<3.4:textproc/py-markdown@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mergedeep>=1.3.4:devel/py-mergedeep@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=20.5:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyyaml_env_tag>=0.1:devel/py-pyyaml_env_tag@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}watchdog>=2.0:devel/py-watchdog@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}yaml>=3.10:devel/py-yaml@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}yaml>=5.1:devel/py-yaml@${PY_FLAVOR}
 
-USES=		cpe python:3.6+
+USES=		cpe python:3.7+
 USE_PYTHON=	distutils concurrent autoplist
 
 NO_ARCH=	yes
 
 OPTIONS_DEFINE=		I18N
 OPTIONS_DEFAULT=	I18N
 
 I18N_DESC=	Support for theme localization
 I18N_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}Babel>=2.9.0:devel/py-babel@${PY_FLAVOR}
 
-.include <bsd.port.mk>
+.include <bsd.port.pre.mk>
+
+.if ${PYTHON_REL} < 30800
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}typing-extensions>=3.10:devel/py-typing-extensions@${PY_FLAVOR}
+.endif
+
+.if ${PYTHON_REL} < 31000
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}importlib-metadata>=4.3:devel/py-importlib-metadata@${PY_FLAVOR}
+.endif
+
+.include <bsd.port.post.mk>
diff --git a/textproc/py-mkdocs/distinfo b/textproc/py-mkdocs/distinfo
index 43443b148b4e..6e0dc018e253 100644
--- a/textproc/py-mkdocs/distinfo
+++ b/textproc/py-mkdocs/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1649270295
-SHA256 (mkdocs-1.3.0.tar.gz) = b504405b04da38795fec9b2e5e28f6aa3a73bb0960cb6d5d27ead28952bd35ea
-SIZE (mkdocs-1.3.0.tar.gz) = 3593181
+TIMESTAMP = 1665826417
+SHA256 (mkdocs-1.4.0.tar.gz) = e5549a22d59e7cb230d6a791edd2c3d06690908454c0af82edc31b35d57e3069
+SIZE (mkdocs-1.4.0.tar.gz) = 3620095