diff --git a/textproc/py-sphinx/Makefile b/textproc/py-sphinx/Makefile
index 52318ed04723..7a5663106ab2 100644
--- a/textproc/py-sphinx/Makefile
+++ b/textproc/py-sphinx/Makefile
@@ -1,5 +1,5 @@
 PORTNAME=	sphinx
-PORTVERSION=	4.5.0
+PORTVERSION=	5.3.0
 PORTEPOCH=	1
 CATEGORIES=	textproc python
 MASTER_SITES=	CHEESESHOP
@@ -17,21 +17,23 @@ WWW=		https://www.sphinx-doc.org/
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}flit>=0:devel/py-flit@${PY_FLAVOR} \
+		pyproject-build:devel/py-build@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}sphinxcontrib-applehelp>=0:textproc/py-sphinxcontrib-applehelp@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sphinxcontrib-devhelp>=0:textproc/py-sphinxcontrib-devhelp@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sphinxcontrib-jsmath>=0:textproc/py-sphinxcontrib-jsmath@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sphinxcontrib-htmlhelp>=2.0.0:textproc/py-sphinxcontrib-htmlhelp@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sphinxcontrib-serializinghtml>=1.1.5:textproc/py-sphinxcontrib-serializinghtml@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sphinxcontrib-qthelp>=0:textproc/py-sphinxcontrib-qthelp@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}Jinja2>=2.3:devel/py-Jinja2@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pygments>=2.0:textproc/py-pygments@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}docutils>=0.14<0.18,1:textproc/py-docutils@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}snowballstemmer>=1.1:textproc/py-snowballstemmer@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}Babel>=1.3:devel/py-babel@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}Jinja2>=3.0:devel/py-Jinja2@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pygments>=2.12:textproc/py-pygments@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}docutils>=0.14,1<0.20,1:textproc/py-docutils@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}snowballstemmer>=2.0:textproc/py-snowballstemmer@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}Babel>=2.9:devel/py-babel@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}alabaster>=0.7<0.8:textproc/py-alabaster@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}imagesize>=0:graphics/py-imagesize@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}imagesize>=1.3:graphics/py-imagesize@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>=2.5.0:www/py-requests@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}packaging>=0:devel/py-packaging@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}packaging>=21.0:devel/py-packaging@${PY_FLAVOR} \
 		${LOCALBASE}/share/certs/ca-root-nss.crt:security/ca_root_nss
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest4-cov>=0:devel/py-pytest4-cov@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}html5lib>=0:www/py-html5lib@${PY_FLAVOR} \
@@ -46,6 +48,16 @@ NO_ARCH=	yes
 # Upstream archive contains files with UTF-8 names (#246618)
 EXTRACT_CMD=	${SETENV} LC_ALL=en_US.UTF-8 /usr/bin/bsdtar
 
+PYDISTUTILS_SETUP=	-c "import setuptools; setuptools.setup()"
+
+CONFIGURE_ENV+=		FLIT_NO_NETWORK=true
+
+CONFIGURE_WRKSRC=	${WRKDIR}/_build
+BUILD_WRKSRC=		${CONFIGURE_WRKSRC}
+INSTALL_WRKSRC=		${CONFIGURE_WRKSRC}
+TEST_WRKSRC=		${CONFIGURE_WRKSRC}
+PYBUILD_OUTDIR=		${WRKDIR}/_pybuild
+
 .include <bsd.port.pre.mk>
 
 .if ${PYTHON_REL} < 31000
@@ -58,4 +70,20 @@ PYTEST_BROKEN_TESTS=	test_latex_images \
 			test_defaults_json \
 			test_anchors_ignored
 
+post-patch:
+	${REINPLACE_CMD} 's@%%VERSION%%@${PORTVERSION}@' ${WRKSRC}/pyproject.toml
+
+## prepare sources, using flit via pybuild
+pre-configure:
+	@(cd ${WRKSRC}; ${SETENV} ${CONFIGURE_ENV} pyproject-build --wheel --outdir ${PYBUILD_OUTDIR} --no-isolation)
+	@(unzip -d ${CONFIGURE_WRKSRC} ${PYBUILD_OUTDIR}/${PYDISTUTILS_PKGNAME}-${PORTVERSION}-py${PYTHON_MAJOR_VER}-*.whl)
+
+## ensure all sphinx resources are installed
+post-install:
+	@(cd ${INSTALL_WRKSRC}; ${COPYTREE_SHARE} . ${STAGEDIR}${PYTHON_SITELIBDIR})
+	@(cd ${INSTALL_WRKSRC}; _TMPF=$$(${MKTEMP} ${WRKDIR}/.plist_tmp.XXXXXX); \
+		cat ${_PYTHONPKGLIST} > $${_TMPF}; \
+		find . -type f | sed 's@./@${PYTHON_SITELIBDIR}/@' >> $${_TMPF}; \
+		${SORT} < $${_TMPF} | uniq > ${_PYTHONPKGLIST})
+
 .include <bsd.port.post.mk>
diff --git a/textproc/py-sphinx/distinfo b/textproc/py-sphinx/distinfo
index 2e9e4229f431..b2ca93b4f3dc 100644
--- a/textproc/py-sphinx/distinfo
+++ b/textproc/py-sphinx/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1654533273
-SHA256 (python/Sphinx-4.5.0.tar.gz) = 7bf8ca9637a4ee15af412d1a1d9689fec70523a68ca9bb9127c2f3eeb344e2e6
-SIZE (python/Sphinx-4.5.0.tar.gz) = 6698212
+TIMESTAMP = 1669461063
+SHA256 (python/Sphinx-5.3.0.tar.gz) = 51026de0a9ff9fc13c05d74913ad66047e104f56a129ff73e174eb5c3ee794b5
+SIZE (python/Sphinx-5.3.0.tar.gz) = 6811365
diff --git a/textproc/py-sphinx/files/patch-pyproject.toml b/textproc/py-sphinx/files/patch-pyproject.toml
new file mode 100644
index 000000000000..6f319278cdef
--- /dev/null
+++ b/textproc/py-sphinx/files/patch-pyproject.toml
@@ -0,0 +1,11 @@
+--- pyproject.toml.orig	2022-10-16 09:53:52 UTC
++++ pyproject.toml
+@@ -75,7 +75,7 @@ dependencies = [
+     "importlib-metadata>=4.8; python_version < '3.10'",
+     "colorama>=0.4.5; sys_platform == 'win32'",
+ ]
+-dynamic = ["version"]
++version = "%%VERSION%%"
+ 
+ [project.optional-dependencies]
+ docs = [