diff --git a/www/py-webob/Makefile b/www/py-webob/Makefile
index e60c94ac156e..985591c91f3d 100644
--- a/www/py-webob/Makefile
+++ b/www/py-webob/Makefile
@@ -1,41 +1,54 @@
 PORTNAME=	webob
-PORTVERSION=	1.8.7
-PORTREVISION=	1
+PORTVERSION=	1.8.9
 CATEGORIES=	www python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
-DISTNAME=	WebOb-${DISTVERSION}
 
 MAINTAINER=	nivit@FreeBSD.org
 COMMENT=	WSGI request and response Python object
 WWW=		https://webob.org/
 
 LICENSE=	MIT
 
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}coverage>=0:devel/py-coverage@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-cov>=0:devel/py-pytest-cov@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest>=0:devel/py-pytest@${PY_FLAVOR}
 
 USES=		python
 
+BUILD_DEPENDS=		${PYTHON_PKGNAMEPREFIX}setuptools>=61:devel/py-setuptools@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pylons-sphinx-themes>=0:textproc/py-pylons-sphinx-themes@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}sphinx>=1.7.5,1:textproc/py-sphinx@${PY_FLAVOR}
-DOCS_VARS=	PYDISTUTILS_BUILD_TARGET+="build_sphinx -a -E"
 DOCSDIR=	${PREFIX}/share/doc/${PYTHON_PKGNAMEPREFIX}${PORTNAME}
 
 OPTIONS_DEFINE=	DOCS
 
 PORTDOCS=	*
 
 NO_ARCH=	yes
-USE_PYTHON=	distutils autoplist
+SUB_FILES=	pyproject.toml
+SUB_LIST=	PORTVERSION=${PORTVERSION}
+USE_PYTHON=	autoplist pep517
+
+pre-configure:
+	[ ! -e ${WRKSRC}/pyproject.toml ] && cp ${WRKDIR}/pyproject.toml ${WRKSRC}
+
+post-build-DOCS-on:
+	${LOCALBASE}/bin/sphinx-build-${PYTHON_VER} -d ${WRKDIR} -b html -E ${WRKSRC}/docs ${WRKSRC}/build/sphinx/html
 
 post-extract-DOCS-on:
 	@(cd ${WRKSRC} && \
-	${LN} -s src/WebOb.egg-info .)
+	${LN} -s src/webob.egg-info .)
 
 post-install-DOCS-on:
 	@(cd ${WRKSRC}/build/sphinx/html && \
 	${COPYTREE_SHARE} . ${STAGEDIR}${DOCSDIR} "! -name .buildinfo -and ! -name objectiv.inv")
 
-.include <bsd.port.mk>
+.include <bsd.port.pre.mk>
+
+.if ${PYTHON_REL} >= 31300
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}legacy-cgi>=0:www/py-legacy-cgi@${PY_FLAVOR}
+.endif
+
+.include <bsd.port.post.mk>
diff --git a/www/py-webob/distinfo b/www/py-webob/distinfo
index d831e0cf7ad8..2de5c84c4381 100644
--- a/www/py-webob/distinfo
+++ b/www/py-webob/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1638441975
-SHA256 (WebOb-1.8.7.tar.gz) = b64ef5141be559cfade448f044fa45c2260351edcb6a8ef6b7e00c7dcef0c323
-SIZE (WebOb-1.8.7.tar.gz) = 278544
+TIMESTAMP = 1750532344
+SHA256 (webob-1.8.9.tar.gz) = ad6078e2edb6766d1334ec3dee072ac6a7f95b1e32ce10def8ff7f0f02d56589
+SIZE (webob-1.8.9.tar.gz) = 279775
diff --git a/www/py-webob/files/patch-docs_conf.py b/www/py-webob/files/patch-docs_conf.py
index 7cfd121ed0af..6a9dcf2dc0e8 100644
--- a/www/py-webob/files/patch-docs_conf.py
+++ b/www/py-webob/files/patch-docs_conf.py
@@ -1,11 +1,23 @@
---- docs/conf.py.orig	2018-04-18 12:16:19 UTC
+--- docs/conf.py.orig	2024-08-14 05:06:46 UTC
 +++ docs/conf.py
-@@ -3,6 +3,8 @@ import sys
+@@ -1,8 +1,10 @@
+-import pkg_resources
++import importlib.metadata as metadata
+ import sys
  import os
  import shlex
  
 +sys.path.insert(0, os.path.abspath('../src'))
 +
  extensions = [
      'sphinx.ext.autodoc',
      'sphinx.ext.intersphinx',
+@@ -27,7 +29,7 @@ author = u'Ian Bicking, Pylons Project, and contributo
+ copyright = u'2018, Ian Bicking, Pylons Project and contributors'
+ author = u'Ian Bicking, Pylons Project, and contributors'
+ 
+-version = release = pkg_resources.get_distribution('webob').version
++version = release = metadata.version("webob")
+ 
+ # The language for content autogenerated by Sphinx. Refer to documentation
+ # for a list of supported languages.
diff --git a/www/py-webob/files/pyproject.toml.in b/www/py-webob/files/pyproject.toml.in
new file mode 100644
index 000000000000..bd54f55daffc
--- /dev/null
+++ b/www/py-webob/files/pyproject.toml.in
@@ -0,0 +1,7 @@
+[build-system]
+requires = ["setuptools >= 61"]
+build-backend = "setuptools.build_meta"
+
+[project]
+name = "webob"
+version = "%%PORTVERSION%%"