diff --git a/net/py-urllib3/Makefile b/net/py-urllib3/Makefile
index 454d8a62bf00..d2d45099d167 100644
--- a/net/py-urllib3/Makefile
+++ b/net/py-urllib3/Makefile
@@ -1,52 +1,52 @@
 PORTNAME=	urllib3
-PORTVERSION=	2.7.0
+PORTVERSION=	2.8.0
 PORTEPOCH=	1
 CATEGORIES=	net python
 MASTER_SITES=	PYPI \
 		https://github.com/urllib3/urllib3/releases/download/${PORTVERSION}/
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	python@FreeBSD.org
 COMMENT=	HTTP library with thread-safe connection pooling, file post, and more
 WWW=		https://urllib3.readthedocs.io/en/stable/ \
 		https://github.com/urllib3/urllib3
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE.txt
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}hatch-vcs>=0.4.0<0.6.0:devel/py-hatch-vcs@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}hatchling>=1.27.0<2:devel/py-hatchling@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools-scm>=8<11:devel/py-setuptools-scm@${PY_FLAVOR}
 TEST_DEPENDS=	${PY_BACKPORTS.ZSTD} \
 		${PYTHON_PKGNAMEPREFIX}brotli>=1.2.0:archivers/py-brotli@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}h2>=4<5:www/py-h2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}httpx>=0.28.1:www/py-httpx@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyopenssl>=25.0.0,1:security/py-pyopenssl@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pysocks>=1.5.6<2.0:net/py-pysocks@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-timeout>=2.3.1:devel/py-pytest-timeout@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}quart>=0.20.0:www/py-quart@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}quart-trio>=0.12.0:www/py-quart-trio@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}trio>=0.27.0:net/py-trio@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}trustme>=1.2.1:security/py-trustme@${PY_FLAVOR}
 
 USES=		cpe python
 USE_PYTHON=	autoplist concurrent cryptography_test pep517 pytest
 
 NO_ARCH=	yes
 PYTEST_IGNORED_TESTS=	test_ssl_read_timeout
 TEST_ENV=	PYTHONPATH=${STAGEDIR}${PYTHON_SITELIBDIR}
 
 SUB_FILES=	pkg-message
 
 CPE_VENDOR=	python
 
 OPTIONS_DEFINE=	BROTLI H2 SOCKS ZSTD
 OPTIONS_DEFAULT=SOCKS
 H2_DESC=	HTTP/2 protocol
 
 BROTLI_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}brotli>=1.0.9:archivers/py-brotli@${PY_FLAVOR}
 H2_RUN_DEPENDS=		${PYTHON_PKGNAMEPREFIX}h2>=4<5:www/py-h2@${PY_FLAVOR}
 SOCKS_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pysocks>=1.5.6<2.0:net/py-pysocks@${PY_FLAVOR}
 ZSTD_RUN_DEPENDS=	${PY_BACKPORTS.ZSTD}
 
 .include <bsd.port.mk>
diff --git a/net/py-urllib3/distinfo b/net/py-urllib3/distinfo
index c47a60628eed..a5375beafeda 100644
--- a/net/py-urllib3/distinfo
+++ b/net/py-urllib3/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1778345126
-SHA256 (urllib3-2.7.0.tar.gz) = 231e0ec3b63ceb14667c67be60f2f2c40a518cb38b03af60abc813da26505f4c
-SIZE (urllib3-2.7.0.tar.gz) = 433602
+TIMESTAMP = 1789834842
+SHA256 (urllib3-2.8.0.tar.gz) = 63bf2ead4c879426ebf22ef2a781eeb4aa3b4ae798a0435506f8687fd5bb9b63
+SIZE (urllib3-2.8.0.tar.gz) = 458972