diff --git a/net/py-urllib3/Makefile b/net/py-urllib3/Makefile
index db00784c8efb..17bdfab67b85 100644
--- a/net/py-urllib3/Makefile
+++ b/net/py-urllib3/Makefile
@@ -1,57 +1,53 @@
 PORTNAME=	urllib3
-PORTVERSION=	2.5.0
+PORTVERSION=	2.6.0
 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} \
-		${PYTHON_PKGNAMEPREFIX}hatchling>=1.6.0<2:devel/py-hatchling@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}hatchling>=1.27.0<2:devel/py-hatchling@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools-scm>=8<10:devel/py-setuptools-scm@${PY_FLAVOR}
-TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}brotli>=1.0.9:archivers/py-brotli@${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} \
-		${PYTHON_PKGNAMEPREFIX}zstandard>=0.18.0:archivers/py-zstandard@${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=	LC_ALL=en_US.UTF-8 \
 		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=	${PYTHON_PKGNAMEPREFIX}zstandard>=0.18.0:archivers/py-zstandard@${PY_FLAVOR}
-
-post-patch:
-	# https://github.com/urllib3/urllib3/pull/3682
-	@${REINPLACE_CMD} -e 's|setuptools-scm>=8,<9|setuptools-scm>=8,<10|' ${WRKSRC}/pyproject.toml
+ZSTD_RUN_DEPENDS=	${PY_BACKPORTS.ZSTD}
 
 .include <bsd.port.mk>
diff --git a/net/py-urllib3/distinfo b/net/py-urllib3/distinfo
index 0c830e9421cf..535b5ab35fc8 100644
--- a/net/py-urllib3/distinfo
+++ b/net/py-urllib3/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1759816994
-SHA256 (urllib3-2.5.0.tar.gz) = 3fc47733c7e419d4bc3f6b3dc2b4f890bb743906a30d56ba4a5bfa4bbff92760
-SIZE (urllib3-2.5.0.tar.gz) = 393185
+TIMESTAMP = 1765033040
+SHA256 (urllib3-2.6.0.tar.gz) = cb9bcef5a4b345d5da5d145dc3e30834f58e8018828cbc724d30b4cb7d4d49f1
+SIZE (urllib3-2.6.0.tar.gz) = 432585